2-Oxo-2-phenylacetic acid (Phenylglyoxylic Acid) by Asch

Reactions (3319)

Yield

Substances (4702)

Citations (815)

Conditions

References

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Rx-ID: 728445

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With ammonium formate; Cp*IrCl(N-(4'-methoxyphenyl)-2-pyridinecarboxamide) complex in methanol

T=60°C; 1.5 h; Inert atmosphereSchlenk tube; Hide Experimental Procedure

Kanto Kagaku Kabushiki Kaisha

Patent: US2010/234596 A1, 2010 ; Location in patent: Page/Page column 14 ; Title/Abstract Full Text Show Details

28:Synthesis of DL-2-phenylglycine

Examples 28 Synthesis of DL-2-phenylglycine 751 mg (5.0 mmol) of benzoyl formate (MW: 150.13), 946 mg (15.0 mmol) of ammonium formate (MW: 63.06), and 5.90 mg (0.01 mmol, S/C=500) of the iridium catalyst Ir-7 (MW: 590.13) were introduced in a 20-mL Schlenk tube and subjected to argon-gas replacement. 5 mL of dehydrated methanol was added and the mixture was stirred while heating at 60° C. for 1.5 hr. After distillation of the solvent, a crystal was collected by filtration, washed with methanol, dried under reduced pressure to give 718 mg of DL-2-phenylglycine (95percent yield). 95%

Stage #1: With ammonium formate in methanol

T=80°C; 0.166667 h; Inert atmosphere; Stage #2: With formic acid; C29H32ClIrNO; triethylamine in methanol

T=80°C; Hide Experimental Procedure

THE UNIVERSITY OF LIVERPOOL; TALWAR, Dinesh; TANG, Weijun; WANG, Chao; VILLA MARCOS, Barbara; XIAO, Jianliang

Patent: WO2013/153407 A1, 2013 ; Location in patent: Paragraph 00163; 00173 ; Title/Abstract Full Text Show Details

3:Example 3 - General procedure for the transfer hydroqenative reductive amination using ammonium formate

Example 3 - General procedure for the transfer hydroqenative reductive amination using ammonium formate Ketone (0.5 mmol) and HCOONH4 (5 mmol) were dissolved in MeOH (2ml) in a carousel reaction tube. The mixture was than degassed and stirred for 10 minutes at 80 °C under nitrogen. HCOOH/NEt3 azeotrope (0.5 ml) and catalyst solution (1 ml) (prepared by dissolving

catalyst (0.5 μηιοΙ) in MeOH (1 ml)) were then introduced. The resulting mixture was stirred at 80 °C for the time indicated. The reaction was quenched with water, basified with aqueous KOH solution and extracted with DCM. The solvent was then removed under vacuum. The crude product was dissolved in ethanol (10 ml) and 6 N HCI solution (5 ml) was than added. The mixture was refluxed for 6 hrs. Ethanol was then removed under vacuum and the resultant aqueous layer was washed with ethyl acetate to remove impurities. The aqueous layer was basified with a KOH solution and extracted with DCM. The organic layers were combined and dried over sodium sulphate. The final product was obtained after the evaporation of solvent under vacuum. 95%

With 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; ammonium formate in methanol

T=80°C; 12 h; Inert atmosphere; chemoselective reaction;

Talwar, Dinesh; Salguero, Noemi Poyatos; Robertson, Craig M.; Xiao, Jianliang

Chemistry - A European Journal, 2014 , vol. 20, # 1 p. 245 - 252 Title/Abstract Full Text View citing articles Show Details

Hide Details 95%

Stage #1: With ammonium formate in methanol

T=80°C; 0.166667 h; Inert atmosphere; Stage #2: With formic acid; 4-methoxy-N-(1-(naphthalen-2-yl)ethylidene)aniline; triethylamine in methanol

T=80°C; Inert atmosphere; Hide Experimental Procedure

Talwar, Dinesh; Tang, Weijun; Wang, Chao; Villa Marcos, Barbara; Xiao, Jianliang

Patent: US2015/80592 A1, 2015 ; Location in patent: Paragraph 0314; 0324 ; Title/Abstract Full Text Show Details

General procedure: Ketone (0.5 mmol) and HCOONH4 (5 mmol) were dissolved in MeOH (2 ml) in a carousel reaction tube. The mixture was than degassed and stirred for 10 minutes at 80° C. under nitrogen. HCOOH/NEt3 azeotrope (0.5 ml) and catalyst solution (1 ml) (prepared by dissolving catalyst (0.5 μmol) in MeOH (1 ml)) were then introduced. The resulting mixture was stirred at 80° C. for the time indicated. The reaction was quenched with water, basified with aqueous KOH solution and extracted with DCM. The solvent was then removed under vacuum. The crude product was dissolved in ethanol (10 ml) and 6 N HCl solution (5 ml) was than added. The mixture was refluxed for 6 hrs. Ethanol was then removed under vacuum and the resultant aqueous layer was washed with ethyl acetate to remove impurities. The aqueous layer was basified with a KOH solution and extracted with DCM. The organic layers were combined and dried over sodium sulphate. This general reaction procedure was then applied to the following reductive amination reactions using catalyst 2c in methanol, the results for which are presented in Table 4D below. 81%

With ammonium formate; [(η5-C5Me5)2Rh2(μ-Cl)2Cl2] in methanol T=50°C; Leuckart-Wallach reaction; 1.5 h;

Kitamura, Masato; Lee, Donghyun; Hayashi, Shinnosuke; Tanaka, Shinji; Yoshimura, Masahiro

Journal of Organic Chemistry, 2002 , vol. 67, # 24 p. 8685 - 8687 Title/Abstract Full Text View citing articles Show Details

29%

With iron(III) sulfide; (NH4)2CO3 in water

T=100°C; 144 h;

Hafenbradi, D.; Keller, M.; Waechtershaeuser, G.; Stetter, K. O.

Tetrahedron Letters, 1995 , vol. 36, # 29 p. 5179 - 5182 Title/Abstract Full Text View citing articles Show Details

With ammonia; iron(II) sulfate

Knoop; Oesterlin

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1927 , vol. 170, p. 199 Full Text Show Details

With D,L-Cysteine; ammonia

Knoop; Oesterlin

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1927 , vol. 170, p. 199 Full Text Show Details

With ammonium hydroxide; palladium

Hydrogenation;

Blasche

Biol. Z., 1933 , vol. 257, p. 14,15 Full Text Show Details

Multi-step reaction with 2 steps 1: ammonium formate / 3,7-dimethyl-10-p-tolyl-5-deazaflavin / 25 h / 120 °C 2: 6 M aq. HCl / Heating View Scheme

Yoneda, Fumio; Kuroda, Kazunori

Journal of the Chemical Society, Chemical Communications, 1982 , # 16 p. 927 - 929 Title/Abstract Full Text View citing articles Show Details

Multi-step reaction with 3 steps 1: NH3 / methanol / Heating 2: HCl / methanol / hygroscopic 3: 55 percent / Bz1QH / methanol / 24 h / Heating; Biomimetic reduction,use of Bz1NH no product View Scheme

Shinkai, Seiji; Hamada, Hisatake; Dohyama, Akihiko; Manabe, Osamu

Tetrahedron Letters, 1980 , vol. 21, p. 1661 - 1664 Title/Abstract Full Text View citing articles Show Details

With α-transaminase

Park, Eul-Soo; Dong, Joo-Young; Shin, Jong-Shik

ChemCatChem, 2013 , vol. 5, # 12 p. 3538 - 3542 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994475

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97%

Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6acac)2; cyclohexylamine; copper(I) bromide in quinoline

T=100°C; 10 h; Inert atmosphereMolecular sieve; Stage #2: With hydrogenchloride in tetrahydrofuran; quinoline; water

T=80°C; 1 h; Inert atmosphere;

Collet, Florence; Song, Bingrui; Rudolphi, Felix; Goossen, Lukas J.

European Journal of Organic Chemistry, 2011 , # 32 p. 6486 - 6501 Title/Abstract Full Text View citing articles Show Details

83%

With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2-one

T=170°C; 16 h;

Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

83%

With 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide; Pd(F6-acac)2 in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h; Reflux; Hide Experimental Procedure

SALTIGO GMBH

Patent: US2009/221832 A1, 2009 ; Location in patent: Page/Page column 3 ; Title/Abstract Full Text Show Details

2; 3:Preparation of 4-methylbenzophenone

Example 2 Preparation of 4-methylbenzophenone Potassium benzoylformate (225.9 mg, 1.2 mmol), bis(1,1,1,5,5,5-hexafluoroacetylacetonato)-palladium (5.2 mg, 0.01 mmol) and copper(I) bromide (21.5 mg, 0.15 mmol) were introduced into a reaction vessel under nitrogen, and a solution of 4-bromotoluene (171.0 mg, 1.0 mmol), tris(o-tolyl)phosphine (6.1 mg, 0.02 mmol) and 1,10-phenanthroline (27 mg, 0.15 mmol) in 1.5 ml of NMP and 0.5 mL of quinoline was added. The reaction mixture was heated under reflux (170° C.) for 16 hours and, after cooling, 20 ml of 1M hydrochloric acid were added, and the aqueous phases were extracted three times with ethyl acetate. The combined organic phases were concentrated and the residue was purified by chromatography. The product was obtained as a yellow oil (163 mg, 83percent yield). The spectroscopic data correspond to those of 4-methylbenzophenone. Hide Details

83%

With copper(I) oxide; bis(acetylacetonato) palladium; copper(l) iodide; 1,10-phenanthroline in 1-methylpyrrolidin-2-one; quinoline

T=50 - 190°C; 0.25 h; Inert atmosphereMicrowave irradiation;

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Rx-ID: 30419352

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Goossen, Lukas J.; Linder, Bettina Zimmermanns Christophe; Rodriguez, Nuria; Lange, Paul P.; Hartung, Jens

Advanced Synthesis and Catalysis, 2009 , vol. 351, # 16 p. 2667 - 2674 Title/Abstract Full Text View citing articles Show Details

91%

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Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F -acac)2; copper(I) bromide in

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Rudolphi, Felix; Song, Bingrui; Goossen, Lukas J.

1-methyl-pyrrolidin-2-one

T=100°C; 16 h; Inert atmosphereMolecular sieve; Stage #2: With potassium tert-butylate in diethyl ether

T=25°C; 1 h; Inert atmosphere;

91%

With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6-acac)2; magnesium trifluoromethane sulfonate; copper(I) bromide in 1-methyl-pyrrolidin-2-one

T=100°C; 16 h; Inert atmosphereMolecular sieve;

Collet, Florence; Song, Bingrui; Rudolphi, Felix; Goossen, Lukas J.

European Journal of Organic Chemistry, 2011 , # 32 p. 6486 - 6501 Title/Abstract Full Text View citing articles Show Details

83%

With copper(I) bromide; 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6-acac)2 in 1-methylpyrrolidin-2-one; cyclohexane

T=100°C; 16 h; Inert atmosphere; Hide Experimental Procedure

Saltigo GmbH

Patent: EP2455364 A1, 2012 ; Location in patent: Page/Page column 8 ;

Advanced Synthesis and Catalysis, 2011 , vol. 353, # 2-3 p. 337 - 342 Title/Abstract Full Text View citing articles Show Details

Title/Abstract Full Text Show Details

Va:

Example (Va); Synthesis of N-(phenyl-(4-tolyl)-methylene)-cyclohexylamine (Va). A mixture of potassium phenyloxoacetate (Ia, 4.52 g, 24.0 mmol), palladium(II) 1,1,1,3,3,3-hexafluoroacetylacetonate (104 mg, 0.20 mmol), copper(I) bromide (430 mg, 3.00 mmol) under nitrogen was treated with a solution of cyclohexylamine (IIa, 2.38 g, 2.75 ml, 24.0 mmol), 4-bromotoluene (IVa, 3.42 g, 2.46 mL, 20.0 mmol), 1,1'-diphenylphosphinoferrocene (114 mg, 0.20 mmol), and 1,10-phenanthroline (541 mg, 3.00 mmol) in 40 mL NMP and 10 mL cyclohexane, excluding air and moisture. The reaction mixture was refluxed at 100 °C for 16 h. It was then washed twice with saturated sodium bicarbonate solution, water, and once with brine, and the aqueous phases were extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and filtered. After removal of the solvent followed by destillation (130 °C / 4x10-3 mbar), the product was obtained as yellow oil (4.58 g, 83percent yield). Hide Details

83%

With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6-acac)2; copper(I) bromide in 1-methylpyrrolidin-2-one; cyclohexane

T=100°C; 16 h; Inert atmosphere; Hide Experimental Procedure

Title/Abstract Full Text Show Details

Va:

Example (Va); Synthesis of N-(phenyl-(4-tolyl)-methylene)-cyclohexylamine (Va). A mixture of potassium phenyloxoacetate (la, 4.52 g, 24.0 mmol), palladium(II) 1, 1, 1,3,3, 3-hexafluoroacetylacetonate (104 mg, 0.20 mmol), copper(I) bromide (430 mg, 3.00 mmol) under nitrogen was treated with a solution of cyclohexylamine (Ila, 2.38 g, 2.75 ml, 24.0 mmol), 4-bromotoluene (IVa, 3.42 g, 2.46 mL, 20.0 mmol), Ι,Γ-diphenylphosphinoferrocene (114 mg, 0.20 mmol), and 1, 10-phenanthroline (541 mg, 3.00 mmol) in 40 mL NMP and 10 mL cyclohexane, excluding air and moisture. The reaction mixture was refluxed at 100 °C for 16 h. It was then washed twice with saturated sodium bicarbonate solution, water, and once with brine, and the aqueous phases were extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulfate and filtered. After removal of the solvent followed by destination (130 °C / 4xl0"3 mbar), the product was obtained as yellow oil (4.58 g, 83percent yield).

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Rx-ID: 27890856

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SALTIGO GMBH; COTTE, Alain; GOTTA, Matthias; GOOssEN, Lukas; RUDOLPHI, Felix; SONG, Bingrui

Patent: WO2012/66134 A1, 2012 ; Location in patent: Page/Page column 10-11 ;

76%

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Stage #1: α-ketophenylacetic acid With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3 h; Stage #2: monopropargylamine With triethylamine in dichloromethane

T=0 - 20°C; 2.66667 h; Hide Experimental Procedure

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ARGENTA DISCOVERY LTD.

Patent: WO2008/96093 A1, 2008 ; Location in patent: Page/Page column 19 ; Title/Abstract Full Text Show Details

Oxalyl chloride (6.1g, 48mmol) was added to a solution of phenylglyoxylic acid (6.Og, 40mmol) and 3 drops of DMF in dry DCM (50ml). The reaction mixture was stirred at room temperature for 3 hours then the solvent was removed. The residue was taken up in dry DCM (50ml) and the solution.was cooled to 0 0C. A mixture of propargyl amine (2.2g, 40 mmoi) and triethylamine (4.05g, 40mmol) was added cautiously over a period of 10 minutes then the mixture was allowed to warm to room temperature. Stirring was continued for 2.5 hours then water (10ml) was added. The mixture was washed with 1 M HCI (2x20ml), sat. sodium hydrogencarbonate (aq.) (2x20ml) then brine. The organic phase was then dried (Na2SO4) and the solvent was removed. The residue was crystallized from cyclohexane to afford the product as a light brown solid.Yield: 5.75g, 76percent LC-MS (Method 3): Rt 2.47 min, m/z 188 [MH+].

76%

Stage #1: α-ketophenylacetic acid With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3 h; Stage #2: monopropargylamine With triethylamine in dichloromethane

ARGENTA DISCOVERY LTD

Patent: WO2008/96128 A1, 2008 ; Location in patent: Page/Page column 43 ;

T=0 - 20°C; 2.66667 h; Hide Experimental Procedure

Title/Abstract Full Text Show Details

Oxalyl chloride (6.1 g, 48 mmol) was added to a solution of phenylglyoxylic acid (6.0 g, 40 mmol) and 3 drops of DMF in dry DCM (50 mL). The reaction mixture was stirred at ambient temperature for 3 hours then the solvent was removed. The residue was taken up in dry DCM (50 mL) and the solution was cooled to 0 0C. A mixture of propargyl amine (2.2 g, 40 mmol) and triethylamine (4.05 g, 40 mmol) was added cautiously over a period of 10 minutes then the mixture was allowed to warm to ambient temperature. Stirring was continued for 2.5 hours then water (10 mL) was added. The mixture was washed with 1 M HCI (2x20 mL), sat. sodium hydrogencarbonate (aq.) (2x20 mL) then brine. The organic phase was then dried (Na2SO4) and the solvent was removed. The residue was crystallized from cyclohexane to afford the product as a light brown solid.Yield: 5.75 g, 76percentLC-MS (Method 3): Rt 2.47 min, m/z 188 [MH+].

76%

Stage #1: α-ketophenylacetic acid With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3 h; Stage #2: monopropargylamine With triethylamine in dichloromethane

T=0 - 20°C; 2.66667 h; Hide Experimental Procedure

ARGENTA DISCOVERY LTD

Patent: WO2008/96143 A1, 2008 ; Location in patent: Page/Page column 20 ; Title/Abstract Full Text Show Details

Oxalyl chloride (6.1 g, 48 mmol) was added to a solution of phenylglyoxylic acid (6.0 g, 40 mmol) and 3 drops of DMF in dry DCM (50 mL). The reaction mixture was stirred at RT for 3 h then the solvent was removed. The residue was taken up in dry DCM (50 mL) and the solution was cooled to 0 0C. A mixture of propargyl amine (2.2 g, 40 mmol) and triethylamine (4.05 g, 40 mmol) was added cautiously over a period of 10 min then the mixture was allowed to warm to RT. Stirring was continued for 2.5 h then water (10 mL) was added. The mixture was washed with 1 M HCl, sat. sodium hydrogencarbonate (aq.), then brine. The organic phase was then dried (Na2SO4) and the solvent was removed. The residue was crystallized from cyclohexane to afford the product as a light brown solid. Yield: 5.75 g, 76percent. LC-MS (Method 3): Rt 2.47 min, m/z 188 [MH+].

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Rx-ID: 728417

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86%

With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane

T=20°C; Inert atmosphereCooling with ice;

Li, Shengkun; Xiao, Taifeng; Li, Dangdang; Zhang, Xumu

Organic Letters, 2015 , vol. 17, # 15 p. 3782 - 3785 Title/Abstract Full Text View citing articles Show Details

84%

With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 31 h; Hide Experimental Procedure

FIRMENICH SA; HERRMANN, Andreas; BERTHIER, Damien; PARET, Nicolas; TRACHSEL, Alain

Patent: WO2014/187833 A1, 2014 ; Location in patent: Page/Page column 23 ; Title/Abstract Full Text Show Details

1:Preparation of isopropyl 2-oxo-2-phenylacetate

A solution of 2-oxo-2-phenylacetic acid (16.21 g, 108 mmol), N,N-dimethylpyridin-4- amine (DMAP) (1.32 g, 10.8 mmol) and propan-2-ol (14.75 mL, 193.0 mmol) in dichloromethane (120 mL) was cooled on an ice-bath before a solution of N,N’15 methanediylidenedicyclohexanamine (DCC) (26.41 g, 128.0 mmol) in dichloromethane(90 mL) was added during 1.5 h. The reaction mixture was stuffed for 30 mm at 0°C, then at 20°C for 29 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3x), HC1 10percent, (3x), and a saturated solution of Na2CO3 (2x). The organic layer was dried (Na2SO4) and concentrated. Columnchromatography (Si02, heptane/ether 4:1) gave 17.40g (84percent) of a slightly yellow oil. ‘H-NMR (400 MHz): ö 8.02-7.97 (m, 2 H); 7.68-7.62 (m, 1 H); 7.55-7.48 (m, 2 H); 5.33(hept., I = 6.3, 1 H); 1.41 (d, I = 6.4, 6 H).‘3C-NMR (100.6 MHz): ö 186.72 (s); 163.66 (s); 134.80 (d); 132.58 (s); 129.96 (d); 128.89 (d); 70.67 (d); 21.74 (q).

73%

With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in benzene

T=0 - 20°C; 12 h; Inert atmosphere;

Chen, Liang-An; Tang, Xiaojuan; Xi, Jianwei; Xu, Weici; Gong, Lei; Meggers, Eric

Angewandte Chemie - International Edition, 2013 , vol. 52, # 52 p. 14021 - 14025 Angew. Chem., 2013 , vol. 125, # 52 p. 14271 - 14275,5 Title/Abstract Full Text View citing articles Show Details

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With sulfuric acid

Huyser,E.S.; Neckers,D.C.

Journal of Organic Chemistry, 1964 , vol. 29, p. 276 - 278 Full Text View citing articles Show Details

Huyser,E.S.; Neckers,D.C.

Journal of Organic Chemistry, 1964 , vol. 29, p. 276 - 278 Full Text View citing articles Show Details

With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in benzene

T=20°C; 12 h; Inert atmosphere;

Martin, Nolwenn J. A.; Cheng, Xu; List, Benjamin

Journal of the American Chemical Society, 2008 , vol. 130, # 42 p. 13862 - 13863 Title/Abstract Full Text View citing articles Show Details

With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in benzene

T=0 - 20°C; 12 h;

Schneider, Jakob F.; Lauber, Markus B.; Muhr, Vanessa; Kratzer, Domenic; Paradies, Jan

Organic and Biomolecular Chemistry, 2011 , vol. 9, # 11 p. 4323 - 4327 Title/Abstract Full Text View citing articles Show Details

With pyridine in dichloromethane

T=0°C; 1 h;

Weng, Jian-Quan; Deng, Qiao-Man; Wu, Liang; Xu, Kai; Wu, Hao; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia

Organic Letters, 2014 , vol. 16, # 3 p. 776 - 779 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 37154526

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82%

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With iodine; oxygen; palladium diacetate; caesium carbonate in 1-methyl-pyrrolidin-2-one

T=45°C; 12 h; Schlenk techniqueSealed tube; Reagent/catalystSolvent; Hide Experimental Procedure

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Gu, Li-Jun; Liu, Ji-Yan; Zhang, Li-Zhu; Xiong, Yong; Wang, Rui

Chinese Chemical Letters, 2014 , vol. 25, # 1 p. 90 - 92 Title/Abstract Full Text View citing articles Show Details

Representative procedure for the synthesis of 3-acylindoles (3)

A 10 mL oven-dried Schlenk tube was charged with phenylglyoxylic acid 1a (49.5mg, 0.33mmol), indole 2a (35.1mg, 0.3mmol), I2 (164.5mg, 0.65mmol), Pd(OAc)2 (10molpercent, 6.7mg, 0.03mmol), Cs2CO3 (292mg, 0.9mmol). The tube was evacuated and filled with O2 (this procedure was repeated three times). Then NMP (1.5mL) were added with a syringe under a counter flow of O2. The tube was sealed with a screw cap. The reaction was stirred at 45°C for 12h, and was then allowed to cool to ambient temperature. The mixture was added 20mL EtOAc, and filtered, washed with water. The organic layers were dried over Na2SO4 and filtered. Solvents were evaporated under reduced pressure. The residue was purified by flash column chromatography with hexane/ethyl acetate to give the corresponding product 3.

79%

With rose bengal in ethanol

T=20°C; 10 h; Molecular sieveIrradiation; Reagent/catalystSolvent; regioselective reaction;

Shi, Qing; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Green Chemistry, 2016 , vol. 18, # 18 p. 4916 - 4923 Title/Abstract Full Text Show Details

57%

With (1,2-dimethoxyethane)dichloronickel(II); Ir(2-(2,4-difluorophenyl)-5-(trifluoromethyl)pyridine)2(4,4’-di-tertbutyl-2,2’-bipyridine)PF6; iodine; caesium carbonate; lithium fluoride; dtbbpy in N,N-dimethyl-formamide

T=20°C; 0.6 h; Schlenk techniqueInert atmosphereIrradiation;

Gu, Lijun; Jin, Cheng; Liu, Jiyan; Zhang, Hongtao; Yuan, Minglong; Li, Ganpeng

Green Chemistry, 2016 , vol. 18, # 5 p. 1201 - 1205 Title/Abstract Full Text View citing articles Show Details

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55%

With copper(II) acetate monohydrate; silver carbonate in dimethyl sulfoxide

T=90°C;

Wang, Cuiping; Wang, Shaoyan; Li, Hua; Yan, Jingbo; Chi, Haijun; Chen, Xichao; Zhang, Zhiqiang

Organic and Biomolecular Chemistry, 2014 , vol. 12, # 11 p. 1721 - 1724 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 728431

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100%

With Dichloromethyl methyl ether

T=50°C; 0.5 h;

Heaney, Frances; Fenlon, Julie; McArdle, Patrick; Cunningham, Desmond

Organic and Biomolecular Chemistry, 2003 , vol. 1, # 7 p. 1122 - 1132 Title/Abstract Full Text View citing articles Show Details

100%

With Dichloromethyl methyl ether in dichloromethane

T=15 - 20°C; 1 h; Inert atmosphere;

Ayitou, Anoklase Jean-Luc; Jesuraj, Josepha L.; Barooah, Nilotpal; Ugrinov, Angel; Sivaguru

Journal of the American Chemical Society, 2009 , vol. 131, # 32 p. 11314 - 11315 Title/Abstract Full Text View citing articles Show Details

95%

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

Senanayake, Chris H.; Fang, Kevin; Grover, Paul; Bakale, Roger P.; Vandenbossche, Charles P.; Wald, Stephen A.

Tetrahedron Letters, 1999 , vol. 40, # 5 p. 819 - 822 Title/Abstract Full Text View citing articles Show Details

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90%

With oxalyl dichloride

90%

With 1,2,3-Benzotriazole; thionyl chloride in dichloromethane

T=20°C; Substitution;

Chaudhari, Sachin S.; Akamanchi, Krishnacharya G.

Synlett, 1999 , # 11 p. 1763 - 1765 Title/Abstract Full Text View citing articles Show Details

70%

With Dichloromethyl methyl ether

T=50°C;

Wipf, Peter; Stephenson, Corey R. J.

Organic Letters, 2003 , vol. 5, # 14 p. 2449 - 2452 Title/Abstract Full Text View citing articles Show Details

56%

With oxalyl dichloride

6 h; Heating;

Harada; Munegumi

Bulletin of the Chemical Society of Japan, 1984 , vol. 57, # 11 p. 3203 - 3209 Title/Abstract Full Text View citing articles Show Details

44%

With thionyl chloride

T=50°C; 6 h;

Becher, Hermann-J.; Fenske, Dieter; Langer, Ernst; Prokscha, Heinz

Monatshefte fuer Chemie, 1980 , vol. 111, p. 749 - 760 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

T=40°C;

Acree

American Chemical Journal, 1913 , vol. 50, p. 393 Full Text Show Details

Fuji, Kaoru; Ueda, Masaru; Sumi, Kenzo; Fujita, Eiichi

Journal of Organic Chemistry, 1985 , vol. 50, # 5 p. 662 - 666 Title/Abstract Full Text View citing articles Show Details

With Dichloromethyl methyl ether

Ottenheijm,H.C.J.; De Man,J.H.M.

Synthesis, 1975 , p. 163 - 164 Full Text View citing articles Show Details

Solladie-Cavallo, Arlette; Bencheqroun, Mohamed

Tetrahedron: Asymmetry, 1991 , vol. 2, # 11 p. 1165 - 1171 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride in benzene

Brown,E.J.D.; Harley-Mason,J.

Journal of the Chemical Society [Section] C: Organic, 1966 , p. 1390 - 1394 Full Text View citing articles Show Details

With pyridine; thionyl chloride in diethyl ether

1.5 h; Ambient temperature;

Nakajima, Masayuki; Anselme, Jean-Pierre

Journal of Organic Chemistry, 1983 , vol. 48, # 9 p. 1444 - 1448 Title/Abstract Full Text View citing articles Show Details

With Dichloromethyl methyl ether

Yield given;

Ojima, Iwao; Yoda, Noriko; Yatabe, Momoko; Tanaka, Toshiyuki; Kogure, Tetsuo

Tetrahedron, 1984 , vol. 40, # 8 p. 1255 - 1268 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; sodium carbonate

2.) THF, overnight; Multistep reaction;

Sayre, L. M.; Larson, D. L.; Takemori, A. E.; Portoghese, P. S.

Journal of Medicinal Chemistry, 1984 , vol. 27, # 10 p. 1325 - 1335 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride in benzene

3 h; Heating;

Burchardt; Geffken

Archiv der Pharmazie, 1988 , vol. 321, # 5 p. 311 - 312 Title/Abstract Full Text View citing articles Show Details

With Dichloromethyl methyl ether

T=50°C; 1 h;

Kiesewetter

Tetrahedron Asymmetry, 1993 , vol. 4, # 10 p. 2183 - 2198 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

Padwa, Albert; Koehler, Konrad F.

Journal of the Chemical Society, Chemical Communications, 1986 , # 10 p. 789 - 790 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

T=60°C;

Chen; Chu; Liao; Tsai; Wang

Tetrahedron Letters, 1999 , vol. 40, # 6 p. 1141 - 1144 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; Chlorination;

Reufer, Christian; Zielinski, Claudia; Schaefer, Hans Juergen; Froehlich, Roland

Acta Chemica Scandinavica, 1999 , vol. 53, # 11 p. 1023 - 1037 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

T=65°C; Chlorination; 1 h;

Chu, Ying-Yuan; Yu, Chia-Sheng; Chen, Chiou-Juy; Yang, Kung-Shuo; Lain, Jung-Chaing; Lin, Chun-Hui; Chen, Kwunmin

Journal of Organic Chemistry, 1999 , vol. 64, # 19 p. 6993 - 6998 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

2 h; Heating;

Chen, Jung-Hsuan; Venkatesham, Uppala; Lee, Li-Chen; Chen, Kwunmin

Tetrahedron, 2006 , vol. 62, # 5 p. 887 - 893 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 4 h;

Szori, Kornel; Balazsik, Katalin; Felfoeldi, Karoly; Bartok, Mihaly

Journal of Catalysis, 2006 , vol. 241, # 1 p. 149 - 154 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride in dichloromethane; N,N-dimethyl-formamide

T=20°C; 2 h;

Koshiishi, Eiji; Hattori, Tetsutaro; Ichihara, Naoki; Miyano, Sotaro

Journal of the Chemical Society. Perkin Transactions 1, 2002 , # 3 p. 377 - 383 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride in dichloromethane

0.5 h; cooling;

Chen, Chien-Tien; Bettigeri, Sampada; Weng, Shiue-Shien; Pawar, Vijay D.; Lin, Ya-Hui; Liu, Cheng-Yuan; Lee, Way-Zen

Journal of Organic Chemistry, 2007 , vol. 72, # 22 p. 8175 - 8185 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3.25 h; Hide Experimental Procedure

ARGENTA DISCOVERY LIMITED

Patent: WO2008/17827 A2, 2008 ; Location in patent: Page/Page column 68-69 ;

1.a:

Title/Abstract Full Text Show Details

Example 1 5-F(/?)-2-(9-fr2-(Cvclohexyi-hvdroxy-phenyl-methyl)-oxazol-5-ylmethvil-methvl- aminol-nonylaminoV1-hvdroxy-ethyll-8-hydroxy-1 /y-quinolin-2-one naphthalene-1 ,5-disulfonate.a) 2-Oxo-2-phenyl-/V-prop-2-ynyl-acetamideOxaly) chloride (19 g, 0.15 mol) was added over 15 min to a solution of phenylglyoxylic acid (20 g, 0.13 mol) and 5 drops of DMF in dry DCM (100 m._). The reaction mixture was stirred at RT for 3 hours after which the solvent was removed in vacuo. The residue was taken up in dry DCM (50 ml_) and the solution was added over 30 minutes to a mixture of propargyl amine (7.3 g, 0.13 mol) and triethylamine (13.5 g, 0.13 mol) in dry DCM (100 ml_) at 0 0C. The mixture was allowed to warm to RT overnight. Water (10 ml_) was added and the mixture was washed twice with 1 M HCI (aq), saturated NaHCO3 (aq), and brine. The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to 100 ml_. Cyclohexane was added until the solution became slightly turbid. The suspension was left at RT for 1 hour. The solid precipitate was collected by filtration and dried at 45 0C in vacuo to afford the title <n="70"/>compound as a light brown crystalline solid. A second crop was collected by re- crystallisation of the mother liquors. Yield: 22 g, 88percent.LC-MS (Method 3): Rt 2.47 min, m/z 188 [MH]+.

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3 h; Hide Experimental Procedure

ARGENTA DISCOVERY LIMITED

Patent: WO2008/99186 A1, 2008 ; Location in patent: Page/Page column 55 ; Title/Abstract Full Text Show Details

2-Oxo-2-phenyl-N-prop-2-ynyl-acetamide; Oxalyl chloride (6.1 g, 48mmol) was added to a solution of phenylglyoxylic acid (6.0 g, 40 mmol) and 3 drops of DMF in dry DCM (50 mL). The reaction mixture was stirred at room temperature for 3 hours then the solvent was removed. The residue was taken up in dry DCM (5OmL) and the solution was cooled to 0 0C. A mixture of propargyl amine (2.2 g, 40 mmol) and triethylamine (4.05 g, 40 mmol) was added cautiously over a period of 10 minutes then the mixture was allowed to warm to room temperature. Stirring was continued for 2.5 hours then water (10 mL) was added. The mixture was washed with 1 M HCI (2x20 mL), sat. NaHCO3 (aq.) (2x20 mL) then brine. The organic phase was dried (Na2SO4), concentrated and the residue crystallized from cyclohexane to afford the title compound as a light brown solid (5.75 g, 76percent). LCMS (Method 2): Rt 2.47 min, m/z 188 [MH+].

With oxalyl dichloride; N,N-dimethyl-formamide

T=0 - 20°C;

Blay, Gonzalo; Hernandez-Olmos, Victor; Pedro, Jose R.

Organic and Biomolecular Chemistry, 2008 , vol. 6, # 3 p. 468 - 476 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride in N,N-dimethyl acetamide

T=-10°C; 1 h; Hide Experimental Procedure

Schwede, Wolfgang; Moeller, Carsten; Schmidt, Anja; Fuhrmann, Ulrike; Rotgeri, Andrea; Kirkland, Thomas Andrew; Wyrwa, Ralf

Patent: US2009/75989 A1, 2009 ; Location in patent: Page/Page column 49 ; Title/Abstract Full Text Show Details

1.a:

Phenylglyoxylic acid (3 g) was dissolved in 50 ml of N,N-dimethylacetamide. At -10° C., 1.75 ml of thionyl chloride were added, and the mixture was stirred at -10° C. for one hour. Then 4.9 g of 6-amino-4-methyl-2,3-benzoxazin-1-one were added in portions. This was followed by stirring for 3 hours (-10° C. to 0° C.). The reaction mixture was then poured into ice-water. The mixture was stirred for 2 hours and filtered with suction. The resulting solid was purified by column chromatography on silica gel with a hexane/ethyl acetate mixture. 4.42 g of product were obtained. 1H NMR (ppm, DMSO-D , 400 MHz): 2.50 (3H); 7.59 (2H); 7.75 (1H); 8.07 (2H); 8.20-8.32 (3H). 6

With dmap; thionyl chloride in dichloromethane

T=-20 - 20°C; Inert atmosphere;

Tomaszewski, Miroslaw J.; Boisvert, Luc; Jin, Shujuan

Tetrahedron Letters, 2009 , vol. 50, # 13 p. 1435 - 1437 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 1 - 2 h; Hide Experimental Procedure

INGENIUM PHARMACEUTICALS GMBH

Patent: WO2009/47359 A1, 2009 ; Location in patent: Page/Page column 110 ; Title/Abstract Full Text Show Details

61:

Example 61 was synthesized according to Method 1 in a yield of 2.5percent, purified by preparative HPLC using Zodiacsil 120-5-C18 column (250 x 32 mm; 10μ), Mobile phase: 0.1 percent formic acid (aq): AcN (25:75) and flow rate: 4 ml/min.1H NMR (400 MHz, CDCI3): δ =

9.53 (s, br., 1 H), 9.01 (s, 1 H), 8.95 (s, 1 H), 8.40 (d, 2H), 7.81 -7.78 (dd, 1 H), 7.69 (t, 1 H), 7.54 (t, 1 H), 7.15 (m, 1 H), 7.00-6.97 (m, 1 H), 3.95 (s, 3H); MS (m/z): 352 (M+H); HPLC (λ = 214 nm, [B]): rt 19.4 min (92.7percent); mp: 146°C.Method 1: (via acid chloride)Thionyl chloride (2 eq) was added dropwise to a cooled mixture of an carboxylic acid RCOOH (1 eq) and 2 drops of dry DMF in dry DCM and stirred at room temperature (or heated at reflux) for 1 -2 h. The volatiles were evaporated and the residual acid chloride dissolved in dry DCM/AcN. In another flask was taken a mixture of amine A (1 eq) and NEt3 (3-4 eq) in dry DCM/AcN and the solution of acid chloride added dropwise at room temperature. The reaction mixture was stirred for 1 - 2 h and quenched into excess of sodium bicarbonate solution. The organic layer was separated and the aqueous layer extracted with DCM. The combined organic layers were washed successively with water and brine, dried (Na2SO4) and concentrated in vacuo to a crude residue. The residue was subjected to either preparative TLC/HPLC to isolate the pure compound.

With Dichloromethyl methyl ether in dichloromethane

T=50°C; Inert atmosphere;

Bou-Hamdan, Farhan R.; Leighton, James L.

Angewandte Chemie, International Edition, 2009 , vol. 48, # 13 p. 2403 - 2406 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3 h; Hide Experimental Procedure

ARGENTA DISCOVERY LTD; ASTRAZENECA AB

Patent: WO2008/96126 A1, 2008 ; Location in patent: Page/Page column 31 ;

Title/Abstract Full Text Show Details

With oxalyl dichloride in dichloromethane; N,N-dimethyl-formamide

T=20°C; 3 h; Inert atmosphere;

Malamas, Michael S.; Erdei, Jim; Gunawan, Iwan; Turner, Jim; Hu, Yun; Wagner, Erik; Fan, Kristi; Chopra, Rajiv; Olland, Andrea; Bard, Jonathan; Jacobsen, Steve; Magolda, Ronald L.; Pangalos, Menelas; Robichaud, Albert J.

Journal of Medicinal Chemistry, 2010 , vol. 53, # 3 p. 1146 - 1158 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C;

Jia, Yi-Xia; Katayev, Dmitry; Kuendig, E. Peter

Chemical Communications, 2010 , vol. 46, # 1 p. 130 - 132 Title/Abstract Full Text View citing articles Show Details

Chiba, Shunsuke; Zhang, Line; Lee, Jian-Yuan

Journal of the American Chemical Society, 2010 , vol. 132, # 21 p. 7266 - 7267 Title/Abstract Full Text View citing articles Show Details

With Dichloromethyl methyl ether in dichloromethane

T=20°C; Inert atmosphere;

Jesuraj, Josepha L.; Sivaguru

Chemical Communications, 2010 , vol. 46, # 26 p. 4791 - 4793 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

12 h; Hide Experimental Procedure

Wyeth

Patent: US2007/27199 A1, 2007 ; Location in patent: Page/Page column 24 ; Title/Abstract Full Text Show Details

37:

Phenylglycolic acid (2) (10.8 g) was dissolved in dichloromethane (200 mL). N,N-Dimethylformamide (100 uL) was added followed by slow addition of oxalyl chloride (72 mL, 2.0 M in dichloromethane) after 12 h the solvent was removed, and the residue was re-dissolved in diethyl ether (100 mL). The insoluble particles were filtered off (Celite) and the solvent was removed leaving brown liquid (11.80 g). 13C NMR: 181.1, 166.7, 135.9, 130.5, 129.4, 129.3

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3 h; Hide Experimental Procedure

ARGENTA DISCOVERY LTD.

Patent: WO2007/17669 A1, 2007 ; Location in patent: Page/Page column 41 ; Title/Abstract Full Text Show Details

Oxalyl chloride (6.1 g, 48mmol) was added to a solution of phenylglyoxylic acid (6.Og, 40mmol) and 3 drops of DMF in dry DCM (50ml). The reaction mixture was stirred at room temperature for 3 hours then the solvent was removed. The residue was taken up in dry DCM (50ml) and the solution was cooled to 0 0C. A mixture of propargyl amine (2.2g, 40 mmol) and triethylamine (4.05g, 40mmol) was added cautiously over a period of 10 minutes then the mixture was allowed to warm to room temperature. Stirring was continued for 2.5 hours then water (10ml) was added. The mixture was washed with 1 M HCI (2x20ml), sat. sodium hydrogencarbonate (aq.) (2x20ml) then brine. The organic phase was then dried (Na2SO4) and the solvent was removed. The residue was crystallized from cyclohexane to afford the product as a light brown solid.Yield: 5.75g, 76percent LC-MS (Method 3): Rt 2.47 min, m/z 188 [MH+].

With thionyl chloride; N,N-dimethyl-formamide in ethyl acetate

T=95°C; 2 h; Hide Experimental Procedure

ONO PHARMACEUTICAL CO., LTD.

Patent: EP1785421 A1, 2007 ; Location in patent: Page/Page column 46 ; Title/Abstract Full Text Show Details

28:

Example 28 (1R,3s,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-6-en-3-yl oxo(phenyl)acetate A catalytic amount of N,N-dimethylformamide was added to an ethyl acetate solution (30 mL) of oxo (phenyl) acetic acid (4.5 g) and thionyl chloride (3.3 mL), followed by stirring at 95° C for 2 hours. After concentration under reduced pressure, the remaining thionyl chloride and hydrogen chloride were removed through azeotropic distillation with use of ethyl acetate. The methylene chloride solution (10 mL) of resultant residue was added to a solution of tropenol (3.5 g) and triethylamine (4.2 mL) in methylene chloride (140 mL), followed by stirring at room temperature overnight. After concentration under reduced pressure, the resultant residue was admixed with an aqueous saturated sodium hydrogencarbonate solution, and extraction was effected with ethyl acetate, followed by washing with water. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The resultant residue was purified on a silica gel column chromatography (methylene chloride:methanol = 6:1) to give the subject title compound (2.6 g) showing the following physico-chemical values: TLC: Rf 0.30 (methylene chloride:methanol:acetic acid = 8:1.5:0.5); 1H-NMR (CDCl ): d 1.79-2.01, 2.39, 2.43-2.58, 3.48-3.65, 5.31, 5.95-6.11, 7.46-7.58, 7.62-7.58, 7.62-7.79, 7.89-8.01. 3

With oxalyl dichloride; N,N-dimethyl-formamide

T=0 - 20°C; 2 h; Hide Experimental Procedure

ARGENTA DISCOVERY LIMITED; ASTRAZENECA AB

Patent: WO2008/23157 A1, 2008 ; Location in patent: Page/Page column 85 ; Title/Abstract Full Text Show Details

14.a:

To a flask containing phenyl glyoxylic acid (4.23 g, 28 mmol), cooled in an ice-bath, was added oxalyl chloride (7 mL). The reaction was initiated by the addition of 1 drop of DMF. The mixture was gradually allowed to warm to room temperature over 2 hours after which the

excess oxalyl chloride was evaporated off under reduced pressure. The crude acid chloride was dissolved in THF (10 mL) and added dropwise to a cooled (0 0C) solution of dimethylamino-acetic acid hydrazide (2.75 g, 24 mmol) and triethylamine (4.9 mL, 35 mmol) in THF (20 mL). This mixture was allowed to warm to room temperature and stirred for 2 hours. Water (50 mL) was added and the mixture extracted with EtOAc (3 x 50 mL). The combined organics were dried over Na2SO4, filtered and evaporated to a yellow solid. Purification on the CombiFlash Companion .(R). system over silica using a 0 - 15 percent MeOH/DCM as eluent gave the title compound as a yellow foam (1.7 g, 24 percent). LC-MS (Method 5): R, 0.32 min, m/z 250 [M+Hf.

With pyridine; thionyl chloride

T=0°C; Inert atmosphere;

Guo, Xingwei; Li, Wenjuan; Li, Zhiping

European Journal of Organic Chemistry, 2010 , # 30 p. 5787 - 5790 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C;

Hu, Jin-Xiu; Wu, Hao; Li, Chuan-Ying; Sheng, Wei-Jian; Jia, Yi-Xia; Gao, Jian-Rong

Chemistry - A European Journal, 2011 , vol. 17, # 19 p. 5234 - 5237 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C;

Zhang, Line; Lee, Jian-Yuan; Yamazaki, Naomi; Chiba, Shunsuke

Synlett, 2011 , # 15 art. no. D14511ST, p. 2167 - 2170 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0°C; Inert atmosphere;

Ylijoki, Kai E. O.; Kuendig, E. Peter

Chemical Communications, 2011 , vol. 47, # 38 p. 10608 - 10610 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride in 1,4-dioxane

T=50°C; 4 h; Inert atmosphere;

Boersch, Christina; Merkul, Eugen; Mueller, Thomas J. J.

Angewandte Chemie - International Edition, 2011 , vol. 50, # 44 p. 10448 - 10452 Title/Abstract Full Text View citing articles Show Details

With Dichloromethyl methyl ether

Fuse, Shinichiro; Masui, Hisashi; Tannna, Akio; Shimizu, Fumihiko; Takahashi, Takashi

ACS Combinatorial Science, 2012 , vol. 14, # 1 p. 17 - 24 Title/Abstract Full Text View citing articles Show Details

With Dichloromethyl methyl ether in dichloromethane

T=50°C; 0.833333 h; Inert atmosphere;

Schoenherr, Heike; Leighton, James L.

Organic Letters, 2012 , vol. 14, # 10 p. 2610 - 2613 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; Inert atmosphere;

Tolstoy, Paeivi; Lee, Samantha X. Y.; Sparr, Christof; Ley, Steven V.

Organic Letters, 2012 , vol. 14, # 18 p. 4810 - 4813,4 Title/Abstract Full Text Show Details

Tolstoy, Päivi; Lee, Samantha X.Y.; Sparr, Christof; Ley, Steven V.

Organic Letters, 2012 , vol. 14, # 18 p. 4810 - 4813 Title/Abstract Full Text View citing articles Show Details

With acetyl chloride in methanol

T=0°C; 6 h; Inert atmosphere; Hide Experimental Procedure

Stella, Selvaraj; Chadha, Anju

Catalysis Today, 2012 , vol. 198, # 1 p. 345 - 352 Title/Abstract Full Text View citing articles Show Details

2.4.2 Amidation of α-keto acids

In a 50 ml double neck RB equipped with a magnetic stirrer, argon inlet adapter, benzoylformic acid (2 mmol) was treated with freshly distilled acetyl chloride (2 equiv.) in dry methanol (6 ml) at 0 °C and stirred for 6 h. The reaction mass was evaporated and redissolved in methanol. To this 30percent NH3 solution (15 ml) was added at 0 °C and stirred for 2 h. During the course of the reaction the product benzoylformamide 3a was formed as white solid. The reaction mass was kept in refrigerator to settle down the product. The solid was filtered, dried and recrystallized from toluene to obtain pure α-keto amide 3a in 41percent yield. The remaining α-keto amides 3b–3e were also prepared by the same procedure. α-keto amides are known to exist as both cis and trans isomers. The NMR data of benzoylformamide 3a taken in CDCl3 was similar to the literature value [50] and showed a single isomer. The intramolecular hydrogen bonding between the amide NH-proton and the keto group in the trans isomer is not disturbed by the non-hydrogen bonding solvent [51] (CDCl3) and it is the predominant isomer in CDCl3. When the spectrum was taken in hydrogen bonding solvent CH3OH-D4, the presence of two isomers was observed due to the slow rotation around the OC–CO single bond [52] which is restricted in non-hydrogen bonding solvent CDCl3 due to the intramolecular hydrogen bonding of the trans isomer. The hydrogen bonding solvent (CH3OH-D4) stabilizes both the cis and trans isomers. The trans–cis isomers of 3a were observed in the ratio 1:0.28 as deduced from the integration of aromatic protons. The ring substituted derivatives of primary α-keto amides 3b–3e are not soluble in chloroform; hence their NMR spectra were recorded in CH3OH-D4. Halogen substituted α-keto amides 3b (p-Cl) and 3c (p-Br) show 2:1 and 2:1.3 trans-cis ratio respectively while the electron donating p-CH3 substituted α-keto amide 3e exhibited less amount of the minor cis isomer in the trans–cis ratio 3:0.26 and only a trace amount of cis isomer was seen in p-OMe substituted α-keto amide 3d. For α-keto amides which exhibit cis–trans isomerism only the 1H NMR values are given below. The major and minor peaks of the same proton are separately listed, if clear separation is obtained.

With thionyl chloride; triethylamine in dichloromethane

T=0 - 20°C; 6.5 h;

Jiang, Lei; Ma, Nan; Qiu, Jun; Zhang, Ronghua

Journal of Chemical Research, 2013 , vol. 37, # 3 p. 143 - 145 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 1 h; Inert atmosphere;

Raghunathan, Ramya; Kumarasamy, Elango; Iyer, Akila; Ugrinov, Angel; Sivaguru

Chemical Communications, 2013 , vol. 49, # 77 p. 8713 - 8715 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

Cheng, Qing-Qing; Zhu, Shou-Fei; Zhang, Yong-Zhen; Xie, Xiu-Lan; Zhou, Qi-Lin

T=0 - 25°C; 7 h; Inert atmosphereSchlenk technique;

Journal of the American Chemical Society, 2013 , vol. 135, # 38 p. 14094 - 14097 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride; sodium hydroxide in N,N-dimethyl acetamide; water

T=-5°C; 0.416667 h; Inert atmosphere;

Cvetovich, Raymond J.; DiMichele, Lisa

Organic Process Research and Development, 2006 , vol. 10, # 5 p. 944 - 946 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 2 h; Inert atmosphere;

Weng, Jian-Quan; Deng, Qiao-Man; Wu, Liang; Xu, Kai; Wu, Hao; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia

Organic Letters, 2014 , vol. 16, # 3 p. 776 - 779 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 3 h;

Shirai, Tomohiko; Ito, Hajime; Yamamoto, Yasunori

Angewandte Chemie - International Edition, 2014 , vol. 53, # 10 p. 2658 - 2661 Angew. Chem., 2014 , vol. 126, # 10 p. 2696 - 2699,4 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; 4 h; Inert atmosphere;

Nicolle, Simon M.; Moody, Christopher J.

Chemistry - A European Journal, 2014 , vol. 20, # 15 p. 4420 - 4425 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; Inert atmosphere;

Enders, Dieter; Stoeckel, Bianca A.; Rembiak, Andreas

Chemical Communications, 2014 , vol. 50, # 34 p. 4489 - 4491 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride in 1,4-dioxane

T=50°C; 4 h; Inert atmosphereSchlenk technique;

Gers, Charlotte F.; Nordmann, Jan; Kumru, Ceyda; Frank, Walter; Mueller, Thomas J. J.

Journal of Organic Chemistry, 2014 , vol. 79, # 8 p. 3296 - 3310 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride in N,N-dimethyl acetamide

T=-15°C; 1 h; TemperatureTime; Hide Experimental Procedure

Joie, Celine; Deckers, Kristina; Enders, Dieter

Synthesis (Germany), 2014 , vol. 46, # 6 art. no. SS-2013-Z0800-OP, p. 799 - 808 Title/Abstract Full Text View citing articles Show Details

α-Ketoamides 1; General Procedure

General procedure: To a solution of phenylglyoxylic acid (1.774 g, 12 mmol, 1 equiv) in N,N-dimethylacetamide (30 mL) cooled to –15 °C, SOCl2 (1.0 mL, 13.8 mmol, 1.15 equiv) was added dropwise. After stirring for 1 h at this temperature, aniline (1.5 mL, 16.7 mmol, 1.4 equiv) was added and the mixture was stirred for 3 h at temperatures between –10 °C and 0 °C, then poured onto a mixture of ice and H2O and stirred at r.t. overnight. The solid formed was dissolved in Et2O (50 mL) and extracted with Et2O (3 × 20 mL). The combined organic layers were washed with H2O and brine, dried (Na2SO4), and concentrated in vacuo before purification by flash column chromatography.

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; Inert atmosphereSchlenk technique;

Ma, Baode; Miao, Tingting; Sun, Yihua; He, Yanmei; Liu, Ji; Feng, Yu; Chen, Hui; Fan, Qing-Hua

Chemistry - A European Journal, 2014 , vol. 20, # 32 p. 9969 - 9978 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; 3 h; Inert atmosphere;

Nicolle, Simon M.; Hayes, Christopher J.; Moody, Christopher J.

Chemistry - A European Journal, 2015 , vol. 21, # 12 p. 4576 - 4579 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

1 h; Hide Experimental Procedure

BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM; READY, Joseph M.; NIJHAWAN, Deepak; GONZALES, Stephen S.; THEODOROPOULOS, Pano

Patent: WO2015/35051 A1, 2015 ; Location in patent: Page/Page column 264 ; Title/Abstract Full Text Show Details

Step 3 Oxalyl chloride (5 eq) was added to a solution of carboxylic acid (1 eq) in CH2CI2 (0.1 M), and then a catalytic amount of DMF was added to the reaction mixture to initiate the reaction and bubbling occurred. The reaction was complete in 1 hour, and the solution was dried with N2 for one hour to give the acid chloride as a yellow oil, which was used immediately in the next step.

With Dichloromethyl methyl ether in dichloromethane

T=40°C; 1 h; Schlenk techniqueInert atmosphere;

Wang, Pan; Feng, Liang-Wen; Wang, Lijia; Li, Jun-Fang; Liao, Saihu; Tang, Yong

Journal of the American Chemical Society, 2015 , vol. 137, # 14 p. 4626 - 4629 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride in dichloromethane

T=20°C; 0.166667 h; Inert atmosphere;

Kou, Kevin G. M.; Longobardi, Lauren E.; Dong, Vy M.

Advanced Synthesis and Catalysis, 2015 , vol. 357, # 10 p. 2233 - 2237 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; 4 h; Inert atmosphere;

Ishida, Naoki; Neas, David; Masuda, Yusuke; Murakami, Masahiro

Angewandte Chemie - International Edition, 2015 , vol. 54, # 25 p. 7418 - 7421 Angew. Chem., 2015 , vol. 127, p. 7526 - 7529,4 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=20°C; 2 h;

Chen, Shengwei; Lou, Qinxin; Ding, Yuyang; Zhang, Shasha; Hu, Wenhui; Zhao, Junling

Advanced Synthesis and Catalysis, 2015 , vol. 357, # 11 p. 2437 - 2441 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; Hide Experimental Procedure

Shin, Inji; Ramgren, Stephen D.; Krische, Michael J.

Tetrahedron, 2015 , vol. 71, # 35 art. no. 26803, p. 5776 - 5780 Title/Abstract Full Text View citing articles Show Details

General Procedure for Amide Coupling.

General procedure: Glyoxylic acid (100 molpercent) was dissolved in CH2Cl2 (0.5 M), and cooled to 0 °C. Oxalylchloride (120 molpercent) was added at 0 °C, then few drops of DMF was added. The mixture was stirred at 0 °C for 30 min, warmed to ambient temperature, and stirred for additional 2–3 h which time no more gas was evaluated. Volatiles were removed in vacuo to give acid chloride. The residue was dissolved to CH2Cl2 (0.5 M), and cooled to 0 °C. 2-Bromoaniline (100 molpercent) was added in one portion, then Et3N (200 molpercent) was dropwised to the flask at 0 °C. The reaction mixture was allowed to stir at ambient temperature overnight. After completion, the mixture was diluted with CH2Cl2, and washed with 1percent HCl. The organic layer was dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography to furnish title compound.

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

2 h;

Jin, Zhichao; Jiang, Ke; Fu, Zhenqian; Torres, Jaume; Zheng, Pengcheng; Yang, Song; Song, Bao-An; Chi, Yonggui Robin

Chemistry - A European Journal, 2015 , vol. 21, # 26 p. 9360 - 9363 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride in dichloromethane; N,N-dimethyl-formamide

T=20°C; 3 h;

Hatano, Miyuki; Nishimura, Takahiro

Angewandte Chemie - International Edition, 2015 , vol. 54, # 37 p. 10949 - 10952 Angew. Chem., 2015 , vol. 127, # 37 p. 11099 - 11102,4 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; 2 h; Hide Experimental Procedure

Wu, Quanquan; Liu, Shulei; Wang, Fangyuan; Li, Qingqing; Cheng, Kangli; Li, Juan; Jiang, Jun

Synlett, 2015 , vol. 26, # 17 art. no. ST-2015-W0427-L, p. 2442 - 2446 Title/Abstract Full Text View citing articles Show Details

Typical Experimental Procedure for Preparation of α-keto esters

General procedure: To a solution of the 2-oxo-2-phenylacetic acid (8.5mmol) in 10.0 mL dry CH2Cl2 at0oC, Oxalyl dichloride (10.2mmol) and a drop of dry DMF were added sequentially.The mixture was then stirred for 2h at room temperature, followed by the remove ofthe solvent and redundant oxalyl dichloride under reduced pressure. Then t-BuOH(17mmol) and pyridine (8.5mmol) were added to the obtained crude acyl chloride indry CH2Cl2 at 0 °C and stirred for 1 h. After that, the reaction mixture was poured intocold water and extracted with CH2Cl2 (3*20 mL). The combined organic phase wasdried over MgSO4, filtrated and concentrated under vacuum. The residue was purifiedby flash chromatography on silica gel, eluting with ethyl acetate/petroleum ether 1:10(v/v) to afford the corresponding products in 80percent yield. 100 %Spectr.

With 1-chloro-1-(dimethylamino)-2-methyl-1-propene in chloroform-d1

T=-20°C; 4 h; Inert atmosphere; Hide Experimental Procedure

Munyemana, Franois; George, Isabelle; Devos, Alain; Colens, Alain; Badarau, Eduard; Frisque-Hesbain, Anne-Marie; Loudet, Aurore; Differding, Edmond; Damien, Jean-Marie; Rmion, Jeanine; Van Uytbergen, Jacqueline; Ghosez, Lon

Tetrahedron, 2016 , vol. 72, # 3 p. 420 - 430 Title/Abstract Full Text View citing articles Show Details

4.2. General procedures for the reaction of a-haloenamines with oxyacids and alcohols

General procedure: Reactions were performed under dry argon atmosphere under magnetic stirring. In procedure A, the alcohol was introduced through a syringe into a 0.5-1 M solution of the α-haloenamine (usually 1.1 equiv) in freshly dried chloroform or dichloromethane or the corresponding deuterated solvents. The reactions were quite exothermic. When performed on a preparative scale, the alcoholwas added at 0 °C, and then the mixture was left at room temperaturefor 0.5-3 h. In procedure B, the α-haloenamine was introduced into a solution of alcohol in the same solvents at 0 °C. It was shown that both procedures gave identical results. In few cases involving the preparation of unstable halides, the halogenation was effected at lower temperature (see Scheme 3) for up to 4 h. Yields were determined after removal of the solvent either by 1H NMR using an added standard (usually benzene or toluene) or by GLC. In some cases the halides were purified by distillation or flash chromatography. The isolated yields were always very close to those measured by NMR or GLC. Most of the halogenation products obtained in this study were known compounds: their spectroscopic properties have been shown to be identical to those reported in the literature and will therefore not been reported here.

With thionyl chloride; triethylamine in dichloromethane

T=0°C; 0.333333 h; Inert atmosphere;

Muthukumar, Alagesan; Mamillapalli, N. Chary; Sekar, Govindasamy

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 4 p. 643 - 652 Title/Abstract Full Text View citing articles Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in dichloromethane

T=0 - 20°C; 3.5 h;

Mal, Kanchan; Naskar, Sandip; Sen, Shovan Kumar; Natarajan, Ramalingam; Das, Indrajit

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 20 p. 3212 - 3230 Title/Abstract Full Text Show Details

With oxalyl dichloride; N,N-dimethyl-formamide in chloroform

T=0 - 20°C; 3 h; Hide Experimental Procedure

CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; ARMANI, Elisabetta; BLACKABY, Wesley; VAN DE PÖEL, Hervé; BAKERGLENN, Charles; TRIVEDI, Naimisha

Patent: WO2016/177849 A1, 2016 ; Location in patent: Page/Page column 59 ; Title/Abstract Full Text Show Details

A mixture of 2-oxo-2-phenyl-acetic acid (4.01 g, 26.7 mmol) and DMF(2 drops) in CHC13 (60 mL) at 0°C was added dropwise with oxalyl chloride (3.62 mL,42.8 mmol) over 10 minutes. The mixture was stirred at 0 °C for a further 30 minutes, then allowed to warm to room temperature and stirred for 2 hours.

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Rx-ID: 37154532

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81%

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With iodine; oxygen; palladium diacetate; caesium carbonate in 1-methyl-pyrrolidin-2-one

T=45°C; 12 h; Schlenk techniqueSealed tube; Hide Experimental Procedure

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Gu, Li-Jun; Liu, Ji-Yan; Zhang, Li-Zhu; Xiong, Yong; Wang, Rui

Chinese Chemical Letters, 2014 , vol. 25, # 1 p. 90 - 92 Title/Abstract Full Text View citing articles Show Details

Representative procedure for the synthesis of 3-acylindoles (3)

General procedure: A 10 mL oven-dried Schlenk tube was charged with phenylglyoxylic acid 1a (49.5mg, 0.33mmol), indole 2a (35.1mg, 0.3mmol), I2 (164.5mg, 0.65mmol), Pd(OAc)2 (10molpercent, 6.7mg, 0.03mmol), Cs2CO3 (292mg, 0.9mmol). The tube was evacuated and filled with O2 (this procedure was repeated three times). Then NMP (1.5mL) were added with a syringe under a counter flow of O2. The tube was sealed with a screw cap. The reaction was stirred at 45°C for 12h, and was then allowed to cool to ambient temperature. The mixture was added 20mL EtOAc, and filtered, washed with water. The organic layers were dried over Na2SO4 and filtered. Solvents were evaporated under reduced pressure. The residue was purified by flash column chromatography with hexane/ethyl acetate to give the corresponding product 3.

71%

With copper(II) acetate monohydrate; silver carbonate in dimethyl sulfoxide; N,N-dimethyl-formamide

T=90°C; 3 h; SolventReagent/catalyst;

Wang, Cuiping; Wang, Shaoyan; Li, Hua; Yan, Jingbo; Chi, Haijun; Chen, Xichao; Zhang, Zhiqiang

Organic and Biomolecular Chemistry, 2014 , vol. 12, # 11 p. 1721 - 1724 Title/Abstract Full Text View citing articles Show Details

55%

With rose bengal in ethanol

T=20°C; 10 h; Molecular sieveIrradiation; regioselective reaction;

Shi, Qing; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Green Chemistry, 2016 , vol. 18, # 18 p. 4916 - 4923 Title/Abstract Full Text Show Details

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Rx-ID: 728390

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92.5%

With sulphate-doped anatase in cyclohexane

RefluxIndustrial scale; Concentration; Hide Experimental Procedure

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China Petroleum & Chemical Corporation; Peng, Xinhua; Jiang, Ou; Ding, Yun; Zheng, Xuegen; Chen, Chengjun; Yu, Shijin; Wu, Xueping

Patent: CN105330547 A, 2016 ; Location in patent: Paragraph 0040; 0041; 0042 ; Title/Abstract Full Text Show Details

4:Example 4

An amount of 1.50 g (10.0 mmol) of benzoylformic acid and 0.42 g (13.0percent) of anhydrous methanol were weighed accuratelyMmol) and 0.12 g of the TiO2 / SO42- catalyst recovered by filtration of the reaction of Example 1 were placedA 50 mL three-necked flask equipped with a magnetic stirrer, a thermometer, a condenser and a water separator,15 mL of cyclohexane was added to the reactor, and then cyclohexane was added to the first drop in a water separatorCyclohexane was dropped into the reactor. The reaction was slowly warmed to reflux with stirringThe reaction was complete by TLC.After the completion of the reaction, the temperature was reduced to room temperature, and the TiO2 / SO42- catalyst was recovered by filtration under reduced pressureMethanol, and the filtrate was collected. The methanol and crude product were removed by distillation under reduced pressure using a rotary evaporatorHPLC was used for the detection (mobile phase chromatographic methanol: the second distilled water = 7:3). The crude product was isolated and purified by column chromatography to give the desired product (eluent: petroleumEther: ethyl acetate = 95: 5, column chromatography silica gel size of 200 ~ 300 mesh), the yield92.5percent, HPLC purity 99.5percent.

89%

With chloro-trimethyl-silane in tetrahydrofuran

T=22°C; 72 h;

Brook, Michael A.; Chan, T. H.

Synthesis, 1983 , # 3 p. 201 - 203 Title/Abstract Full Text Show Details

With hydrogenchloride

Kohler, Corson

Journal of the American Chemical Society, 1923 , vol. 45, p. 1983 Full Text Show Details

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With hydrogenchloride

Claisen

Chemische Berichte, 1879 , vol. 12, p. 633 Chemische Berichte, 1877 , vol. 10, p. 1663 Full Text Show Details

With hydrogen cation

Dao, Duc Hai; Okamura, Mutsuo; Akasaka, Takeshi; Kawai, Yasushi; Hida, Kouichi; Ohno, Atsuyoshi

Tetrahedron Asymmetry, 1998 , vol. 9, # 15 p. 2725 - 2737 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

T=-10 - 20°C; Esterification; 0.5 h;

Kayser, Margaret M.; Mihovilovic, Marko D.; Kearns, Jeff; Feicht, Anton; Stewart, Jon D.

Journal of Organic Chemistry, 1999 , vol. 64, # 18 p. 6603 - 6608 Title/Abstract Full Text View citing articles Show Details

With sulfuric acid

Malpica; Calzadilla

Journal of Physical Organic Chemistry, 2005 , vol. 18, # 9 p. 945 - 949 Title/Abstract Full Text View citing articles Show Details

87.3 %Chromat.

With sulfuric acid in cyclohexane; water

T=82°C; 3.3 h;

Dai, Zhihong; Peng, Xinhua; Dong, Xiongzi; Shi, Chunjie; Rong, Yuan

Asian Journal of Chemistry, 2012 , vol. 24, # 11 p. 4979 - 4985 Title/Abstract Full Text View citing articles Show Details

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96%

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With carbazic acid

T=90°C; 3 h; Green chemistry; Reagent/catalystSolventTemperature; Hide Experimental Procedure

Rx-ID: 35121173

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Lee, Byeongno; Kang, Philjun; Lee, Kyu Hyung; Cho, Jaeheung; Nam, Wonwoo; Lee, Won Koo; Hur, Nam Hwi

Tetrahedron Letters, 2013 , vol. 54, # 11 p. 1384 - 1388 Title/Abstract Full Text View citing articles Show Details

3. General procedure for the solid state or solvent-free reactions between 1a and di-carbonyl compounds.

General procedure: A 10.0 mmol for α-keto acid compound or a 5.2 mmol for β-diketones or α-keto acids was mixed with 0.40 g of hydrazinium carboxylate (1a, 5.2 mmol), respectively. (For solid di-carbonyl compound, the mixture was ground using a pestle and a mortar.) The mixture was stored in a closed vial, and then heated to 70 – 90 °C until the reaction was complete. Complete conversion to related product was dependent upon the nature of di-carbonyl compounds. Typically, those di-carbonyl compounds take about <3 h to complete the reactions. CO2 and water were released during the reaction. All products obtained from the reactions of 1a with di-carbonyl compounds were basically characterized by 1H and 13C NMR spectroscopy. The products have over 97percent of purity of reaction mixture based on 1H NMR spectroscopy and isolation yields are over 97percent based on di-carbonyl compounds. The melting points, elemental analysis and UV-Vis spectra for all azines, pyrazoles and pyridazinones, were measured after purification using appropriate solvent.

96%

With carbazic acid in neat (no solvent) T=90°C; 3.16 h; SolventTemperatureReagent/catalyst; Hide Experimental Procedure

Sogang University Academic Cooperation; Haw, Nam Hwe; Lee, Byung Noh; Lee, Won Gu

Patent: KR101483445 B1, 2015 ; Location in patent: Paragraph 0172-0174 ;

Title/Abstract Full Text Show Details

1:Example 1

50.0 mmole (3.8 g) of solid hydrazine carboxylate (H3N + NHCO2-) and 100.0 mmol (15.0 g) of 2-oxo-2-phenylacetic acid were mixed in a mortar for 10 minutes without a solvent and allowed to stand at 90 °C for 3 hours. The reaction products were analyzed by 400 MHz NMR, GC / MS, IR, UV-Vis. And elemental analysis. The product analysis results (2Z, 2'Z)-2,2'-(hydrazine-1,2-ylidene)bis(2-phenylacetic acid), selectivity is> 99percent, the yield was more than 96percent.

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Rx-ID: 1513565

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100%

With NH4S2O8; sulfuric acid; silver nitrate in dichloromethane; water

T=40°C; 2.5 h;

Fontana, Francesca; Minisci, Francesco; Barbosa, Maria Claudia Nogueira; Vismara, Elena

Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2866 - 2869 Title/Abstract Full Text View citing articles Show Details

91%

Stage #1: With (NH4)2S2O8; sulfuric acid; silver nitrate in dichloromethane; water

T=50°C; 2 h; Stage #2: With water; sodium hydrogencarbonate in dichloromethane

MOGAM BIOTECHNOLOGY RESEARCH INSTITUTE

Patent: WO2008/85008 A1, 2008 ; Location in patent: Page/Page column 27-28 ;

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Title/Abstract Full Text Show Details

Example 7: Preparation of l-phenylimidazo[l,5-a]pyrazine-3(2H)-thione; SUBSTITUTE SHEET (RULE 26) <n="30"/>To a mixture of pyrazine (610 mg, 7.62 mmol), phenylglyoxylic acid (3.429 g, 3 equiv), C-H2SO4 (0.4 mL, 1 equiv), AgNO3 (129 mg, 0.1 equiv), (NH4)ZS2O8 (5.22 g, 3 equiv) in CH2C12/H2O (=1/1, 60 mL) was stirred at 50 0C for 2 h. The reaction mixture was diluted with CH2Cl2 and washed with aqueous NaHCO3. The water layer was extracted with CH2Cl2 one more time. The organic layer was dried over MgSO4, filtered, and

evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexanes: ethyl acetateidichloromethane = 5: 1 :2) to give ketone (1.27 g, 91percent). This ketone (801 mg, 4.35 mmol) in EtOHTH2O (=10:1, 10 mL) were added hydroxylamine hydrochloride (393 mg, 1.3 equiv) and NaOH (226 mg, 1.3 equiv) at rt. After being stirred at rt overnight, the mixture was concentrated in vacuo. The residue was diluted with CH2Cl2 and washed with water. The water layer was extracted with CH2Cl2 one more time. The combined organic layers were dired over MgSO4, filtered, and evaporated under reduced pressure to give the crude oxime, which was used for the next step without further purification. To this oxime in MeOH (15 mL) were added Zn powder (853mg, 3 equiv) and AcOH (0.25 mL, 1 equiv) at rt. After being heated to reflux for 2 h, the mixture was cooled to rt. The reaction mixture was filtered through a pad of Celite and the filtrate was evaporated in vacuo. The residue was diluted with CH2Cl2 and washed with aqueous NaHCO3. The insoluble salt was filtered out. The organic layer was dried over MgSO4,SUBSTITUTE SHEET (RULE 26) <n="31"/>filtered, and evaporated to give a crude mixture which was further purified by silica gel column chromatography (hexanes: ethyl acetate = 1 :1 to ethyl acetate only to dichloromethane:methanol = 10:1) to afford amine (330 mg, 41percent). To a solution of amine (255 mg, 1.378mmol) in MeOH (7 mL) were added CS2 (0.6 mL, 7.2 equiv) and Et3N (0.4 mL, 2 equiv) at it. After being heated to reflux overnight, the mixture was cooled to it. The reaction mixture was concentrated in vacuo and the residue was suspended in CH2C12/H2O. The solid was filtered and dried to give l-phenylimidazo[l,5-a]pyrazine-3(2H)-thione (250 mg, 80percent). 300 MHz 1H NMR (DMSO-d6) 9.10 (IH, d, J= 1.5 Hz), 7.94 (IH, dd, J= 5.1, 1.5 Hz), 7.83 (2H, d, J - 6.9 Hz), 7.60-7.35 (4H, m).

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Rx-ID: 4785993

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93%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=20°C; 48 h; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 17 ;

Title/Abstract Full Text Show Details

1:Preparation of (Z)-3-nonenyl 2-oxo-2-phenylacetate

General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product. Preparation of (Z)-3-hexenyl 2-oxo-2-phenylacetate (0119) As described above in the general method with (Z)-3-hexen-1-ol (6.61 g, 50.0 mmol, 1.3 eq.) stirred at room temperature for 48 h. Column chromatography (SiO2, heptane/ether 7:3) gave 8.04 g (93percent) of a yellow oil. (0120) 1H-NMR (360 MHz): δ 8.04-7.98 (m, 2H); 7.69-7.62 (m, 1H); 7.55-7.47 (m, 2H); 5.61-5.51 (m, 1H); 5.41-5.31 (m, 1H); 4.39 (t, J=6.9, 2H); 2.58-2.49 (m, 2H); 2.12-2.01 (m, 2H); 0.95 (t, J=7.5, 3H). (0121) 13C-NMR (90.6 MHz): δ 186.36 (s); 163.87 (s); 135.39 (d); 134.90 (d); 132.49 (s); 130.07 (d); 128.89 (d); 122.87 (d); 65.63 (t); 26.64 (t); 20.66 (t); 14.15 (q).

Hu, Shengkui; Neckers, Douglas C.

Journal of Organic Chemistry, 1997 , vol. 62, # 20 p. 6820 - 6826 Title/Abstract Full Text View citing articles Show Details

2 h; Heating; Yield given;

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Rx-ID: 11199576

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95%

With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C;

Levrand, Barbara; Herrmann, Andreas

Chimia, 2007 , vol. 61, # 10 p. 661 - 664 Title/Abstract Full Text View citing articles Show Details

95%

With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; Hide Experimental Procedure

Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 17 ; Title/Abstract Full Text Show Details

1:Preparation of 2-phenylethyl 2-oxo-2-phenylacetate

General procedure: General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50-100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product. Preparation of 2-phenylethyl 2-oxo-2-phenylacetate (0116) As described above in the general method with 2-phenylethanol (5.00 g, 41.0 mmol). Column chromatography (SiO2, heptane/ether 8:2 to 7:3) gave 5.52 g (95percent) of a yellow oil. (0117) 1H-NMR (360 MHz): δ 7.89-7.82 (m, 2H); 7.66-7.58 (m, 1H); 4.49-7.40 (m, 2H); 7.36-7.20 (m, 5H); 4.62 (t, J=7.1, 2H); 3.08 (t, J=6.9, 2H). (0118) 13C-NMR (90.6 MHz): δ 186.28 (s); 163.72 (s); 136.96 (s); 134.87 (d); 132.32 (s); 130.02 (d); 129.01 (d); 128.85 (d); 128.68 (d); 126.86 (d); 66.40 (t); 34.93 (t).

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Rx-ID: 27994479

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99%

With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

94%

Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6acac)2; cyclohexylamine; copper(I) bromide in quinoline

T=100°C; 10 h; Inert atmosphereMolecular sieve; Stage #2: With hydrogenchloride in tetrahydrofuran; quinoline; water

T=80°C; 1 h; Inert atmosphere;

Collet, Florence; Song, Bingrui; Rudolphi, Felix; Goossen, Lukas J.

European Journal of Organic Chemistry, 2011 , # 32 p. 6486 - 6501 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 35284521

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81%

With di-tert-butyl peroxide; trimethylpyruvic acid; copper(ll) bromide in toluene

T=110°C; 18 h; Reagent/catalystSolvent;

Li, Dengke; Wang, Min; Liu, Jie; Zhao, Qiong; Wang, Lei

Chemical Communications, 2013 , vol. 49, # 35 p. 3640 - 3642 Title/Abstract Full Text View citing articles Show Details

80%

With di-tert-butyl peroxide; copper diacetate

T=110°C; 3 h; Schlenk techniqueInert atmosphere; ConcentrationReagent/catalyst;

Wang, Hua; Guo, Li-Na; Duan, Xin-Hua

Organic and Biomolecular Chemistry, 2013 , vol. 11, # 28 p. 4573 - 4576 Title/Abstract Full Text View citing articles Show Details

70%

With hydrogenchloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide in 1,4-dioxane

T=120°C; 3 h; Hide Experimental Procedure

Bannwart, Linda; Abele, Stefan; Tortoioli, Simone

Synthesis (Germany), 2016 , vol. 48, # 13 art. no. SS-2016-T0107-OP, p. 2069 - 2078 Title/Abstract Full Text View citing articles Show Details

N,N-Dimethyl-2-oxo-2-phenylacetamide (14)

General procedure: A 20 mL Radleys Carousel screw-capped glass tube was charged with carboxylic acid (2 mmol, 1.0 equiv), DMF (1.2 mL), T3P® in DMF 50percent(1.28 mL, 1.4 g, 1.1 equiv) and HCl (4 M in dioxane, 0.25 mL, 1.0mmol, 0.5 equiv) at r.t. The mixture was heated to 130 °C (ca. 120 °C internal) and stirred until the conversion according to LC-MS or TLCwas ≥95percent. The solution was quenched at 10 °C with aq half-saturated Na2CO3 (5 mL; caution: gas evolution) and extracted with i-PrOAc (10mL and 2 × 5 mL or until no product was present in the aqueousphase). Combined organic phases were dried over MgSO4 and concentratedunder reduced pressure. The crude product was purified bychromatography on silica gel as described below. N,N-Dimethyl-2-oxo-2-phenylacetamide (14) The reaction was performed according to the general procedure with2-oxo-2-phenylacetic acid as starting material. After work-up, the crude material was absorbed on Celite, concentrated to dryness andpurified by chromatography on silica gel (20 g Isolute SPE column,Flash Si II; heptane–EtOAc, 8:1 to 1:1) to give 14.Yield: 248 mg (70percent); colorless oil.1H NMR (500 MHz, CDCl3): δ = 7.93 (dd, J = 1.2, 7.2 Hz, 2 H), 7.61–7.64(m, 1 H), 7.48–7.51 (m, 2 H), 3.05–3.10 (m, 3 H), 2.90–2.96 (m, 3 H).13C NMR (125 MHz, CDCl3): δ = 191.85, 167.06, 134.77, 133.04,129.64, 129.04, 37.05, 33.99.MS: m/z = 178.23 [M + 1]+

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Rx-ID: 36266375

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88%

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With triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) in 1,4-dioxane

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Gruenberg, Matthias F.; Goossen, Lukas J.

T=100°C; 16 h; Inert atmosphere; Reagent/catalystSolvent; Hide Experimental Procedure

Journal of Organometallic Chemistry, 2013 , vol. 744, p. 140 - 143 Title/Abstract Full Text View citing articles Show Details

4.2 Standard procedure for the synthesis of α,β-unsaturated ketones from α-oxocarboxylic acids

General procedure: A 20 mL crimp-cap vessel was charged with bis(dibenzylideneacetone)palladium(0) (28.8 mg, 0.05 mmol) and triphenylphosphine (91.8 mg, 0.35 mmol). A solution of the α-oxocarboxylic acid (1a–l) (1.00 mmol) in 1,4-dioxane (8 mL) and allyl alcohol (2) (104 μL, 1.50 mmol) were added via syringe. The reaction mixture was stirred at 100 °C for 16 h and was then cooled to room temperature. The solvent was removed in vacuo (40 °C, 100 mbar) and the remaining residue was further purified by flash chromatography (SiO2, ethyl acetate/hexane (1:10)), yielding the corresponding ketones 4a–l (63–96percent).

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Rx-ID: 37154531

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84%

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With iodine; oxygen; palladium diacetate; caesium carbonate in 1-methyl-pyrrolidin-2-one

T=45°C; 12 h; Schlenk techniqueSealed tube; Hide Experimental Procedure

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Gu, Li-Jun; Liu, Ji-Yan; Zhang, Li-Zhu; Xiong, Yong; Wang, Rui

Chinese Chemical Letters, 2014 , vol. 25, # 1 p. 90 - 92 Title/Abstract Full Text View citing articles Show Details

Representative procedure for the synthesis of 3-acylindoles (3)

67%

With rose bengal in ethanol

T=20°C; 10 h; Molecular sieveIrradiation; regioselective reaction;

Shi, Qing; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Green Chemistry, 2016 , vol. 18, # 18 p. 4916 - 4923 Title/Abstract Full Text Show Details

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Rx-ID: 37154533

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85%

With rose bengal in ethanol

T=20°C; 10 h; Molecular sieveIrradiation; regioselective reaction;

Shi, Qing; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Green Chemistry, 2016 , vol. 18, # 18 p. 4916 - 4923 Title/Abstract Full Text Show Details

75%

With iodine; oxygen; palladium diacetate; caesium carbonate in 1-methyl-pyrrolidin-2-one

T=45°C; 12 h; Schlenk techniqueSealed tube; Hide Experimental Procedure

Gu, Li-Jun; Liu, Ji-Yan; Zhang, Li-Zhu; Xiong, Yong; Wang, Rui

Chinese Chemical Letters, 2014 , vol. 25, # 1 p. 90 - 92 Title/Abstract Full Text View citing articles Show Details

Representative procedure for the synthesis of 3-acylindoles (3)

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Rx-ID: 27994469

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87%

Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6acac)2; cyclohexylamine; copper(I) bromide in quinoline

T=100°C; 10 h; Inert atmosphereMolecular sieve; Stage #2: With hydrogenchloride in tetrahydrofuran; quinoline; water

T=80°C; 1 h; Inert atmosphere;

Collet, Florence; Song, Bingrui; Rudolphi, Felix; Goossen, Lukas J.

European Journal of Organic Chemistry, 2011 , # 32 p. 6486 - 6501 Title/Abstract Full Text View citing articles Show Details

82%

With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 37154535

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88%

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With iodine; oxygen; palladium diacetate; caesium carbonate in 1-methyl-pyrrolidin-2-one

T=45°C; 12 h; Schlenk techniqueSealed tube; Hide Experimental Procedure

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Gu, Li-Jun; Liu, Ji-Yan; Zhang, Li-Zhu; Xiong, Yong; Wang, Rui

Chinese Chemical Letters, 2014 , vol. 25, # 1 p. 90 - 92 Title/Abstract Full Text View citing articles Show Details

Representative procedure for the synthesis of 3-acylindoles (3)

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Rx-ID: 39180167

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83%

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

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Rx-ID: 39180168

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81%

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

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97.7%

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Stage #1: thiosemicarbazide; α-ketophenylacetic acid in water

0.25 h; Heating / reflux; Stage #2: With potassium hydroxide in methanol; water

T=80°C; 48 h; Stage #3: methyl iodide in methanol; water

T=40°C; 0.5 h; Hide Experimental Procedure

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INCYTE CORPORATION

Patent: US2008/39457 A1, 2008 ; Location in patent: Page/Page column 31 ; Title/Abstract Full Text Show Details

44.1:

A mixture of thiosemicarbazide (1.8 g, 0.020 mol) and benzoylformic acid (3.0 g, 0.020 mol) in water (50 mL) was heated under reflux for 15 min. Then potassium hydroxide (1.5 g, 0.027 mol) in methanol (50 mL) was added at 80° C. The reaction mixture was stirred and heated at 80° C. for 2 days. After cooling to 35° C., methyl iodide (1.4 mL, 0.022 mol) was added. The reaction mixture was stirred at 40° C. for 30 min. The mixture was concentrated. The precipitate formed was collected by filtration, washed with water, and dried under vacuum to afford the desired product (4.3 g, 97.7percent). Analytical LCMS: (M+H)+=220.1.

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Rx-ID: 27994480

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88%

Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6acac)2; cyclohexylamine; copper(I) bromide in quinoline

T=100°C; 10 h; Inert atmosphereMolecular sieve; Stage #2: With hydrogenchloride in tetrahydrofuran; quinoline; water

T=80°C; 1 h; Inert atmosphere;

Collet, Florence; Song, Bingrui; Rudolphi, Felix; Goossen, Lukas J.

European Journal of Organic Chemistry, 2011 , # 32 p. 6486 - 6501 Title/Abstract Full Text View citing articles Show Details

72%

With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 29068738

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66%

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With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine in dichloromethane

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LEAD THERAPEUTICS, INC.

Patent: US2010/35883 A1, 2010 ;

Location in patent: Page/Page column 87 ;

T=20°C; Hide Experimental Procedure

Title/Abstract Full Text Show Details

118A:

To a solution of 4-aminoisobenzofuran-1(3H)-one (4.0 g, 26.8 mmol), 2-oxo-2-phenylacetic acid (4.1 g, 26.8 mmol), and HBTU (15.2 g, 40.2 mmol) in dichloromethane (240 mL) was added TEA (8 mL). The reaction mixture was stirred at room temperature overnight. The resulting mixture was added water and adjusted to pH=6-7 with 1percent aq. HCl, and then was filtered. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was evaporated and the crude product was purified by gradient chromatography (silica gel, petroleum ether/ethyl acetate 6:1 to 3:1) to give the title compound (5.0 g, yield 66percent). LC-MS (ESI) m/z: 282(M+1)+.

66%

Stage #1: With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine in dichloromethane

T=20°C; Stage #2: With hydrogenchloride in water

pH=6 - 7; Hide Experimental Procedure

BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHU, Daniel

Patent: WO2011/130661 A1, 2011 ; Location in patent: Page/Page column 169-170 ; Title/Abstract Full Text Show Details

118A:

Example 1 18A2-Oxo-N-(l-oxo- l,3-dihydroisobenzofuran-4-yl)-2-phenylacetamide[00735] To a solution of 4-aminoisobenzofuran-l(3H)-one (4.0 g, 26.8 mmol), 2-oxo-2-phenylacetic acid (4.1 g, 26.8 mmol), and HBTU (15.2 g, 40.2 mmol) in dichloromethane (240 mL) was added TEA (8 mL). The reaction mixture was stirred at room temperature overnight. The resulting mixture was added water and adjusted to pH 6-7 with 1percent aq. HCl, and then was filtered. The filtrate was extracted with ethyl acetate. The ethyl acetate layer was evaporated and the crude product was purified by gradient chromatography (silica gel, petroleum ether / ethyl acetate 6: 1 to 3: 1) to give the title compound (5.0 g, yield 66percent). LC-MS (ESI) m/z: 282(M+1)+.

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Rx-ID: 37154534

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62%

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With iodine; oxygen; palladium diacetate; caesium carbonate in 1-methyl-pyrrolidin-2-one

T=45°C; 12 h; Schlenk techniqueSealed tube; Hide Experimental Procedure

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Gu, Li-Jun; Liu, Ji-Yan; Zhang, Li-Zhu; Xiong, Yong; Wang, Rui

Chinese Chemical Letters, 2014 , vol. 25, # 1 p. 90 - 92 Title/Abstract Full Text View citing articles Show Details

Representative procedure for the synthesis of 3-acylindoles (3)

49%

With copper (II) acetate monohydrate; silver carbonate in dimethyl sulfoxide

T=90°C;

Wang, Cuiping; Wang, Shaoyan; Li, Hua; Yan, Jingbo; Chi, Haijun; Chen, Xichao; Zhang, Zhiqiang

Organic and Biomolecular Chemistry, 2014 , vol. 12, # 11 p. 1721 - 1724 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 39105907

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89%

With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in dichloromethane

T=20°C; 6 h; Cooling with ice; Hide Experimental Procedure

FIRMENICH SA; HERRMANN, Andreas; BERTHIER, Damien; PARET, Nicolas; TRACHSEL, Alain

Patent: WO2014/187833 A1, 2014 ; Location in patent: Page/Page column 24 ; Title/Abstract Full Text Show Details

1:Preparation of ethane-1,2-diyl bis(2-oxo-2-phenylacetate)

A solution of 2-oxo-2-phenylacetic acid (14.50 g, 96.5 mmol), DMAP (6.30 g, 51.5mmol) and ethylene glycol (4.00 g, 64.4 mmol) in dichloromethane (75 mL) was cooledon an ice-bath before a solution of DCC (14.60 g, 71.0 mmol) in dichloromethane (50 mL) was added. Then more 2-oxo-2-phenylacetic acid (14.50 g, 96.5 mmol) in dichloromethane (20 mL), DMAP (6.30 g, 51.5 mmol) in dichloromethane (20 mL) and DCC (14.60 g, 71.0 mmol) in dichloromethane (35 mL) was added. The reaction mixturewas left warming to room temperature and stirred for 6 h. The precipitate formed in the reaction was filtered off and washed with dichloromethane. The filtrate was washed with HC1 10percent, (2x), a saturated solution of Na2CO3 (2x) and a saturated solution of NaC1 (2x). The organic layer was dried (Na2SO4) and concentrated to give 18.80 g of the crude product. Column chromatography of 9.40 g (Si02, heptane/ethyl acetate 1:1) gave 7.16 g(89percent) of a white solid.‘H-NMR (400 MHz): ö 8.03-7.97 (m, 4 H); 7.67-7.61 (m, 2 H); 7.52-7.45 (m, 4 H); 4.74 (s,4H).‘3C-NMR (100.6 MHz): ö 185.55 (s); 163.26 (s); 135.13 (d); 132.19 (s); 130.10 (d); 128.99 (d); 62.99 (t).

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Rx-ID: 39366654

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96%

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With dipotassium peroxodisulfate; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 21 h; Sealed tube; ConcentrationReagent/catalyst; Hide Experimental Procedure

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Gong, Wei-Jie; Liu, De-Xian; Li, Fei-Long; Gao, Jun; Li, Hong-Xi; Lang, Jian-Ping

Tetrahedron, 2015 , vol. 71, # 8 p. 1269 - 1275 Title/Abstract Full Text View citing articles Show Details

General procedure for the acylation of benzothiophene or benzofuran with α-oxocarboxylic acid

General procedure for the acylation of benzothiophene or benzofuran with α-oxocarboxylic acid A sealed reaction tube equipped with a magnetic stirring bar was charged with 2-(benzothiophen-2-yl)pyridine (0.1 mmol), α-oxocarboxylic acids (0.2 mmol), K2S2O8 (0.2 mmol), tetrabutyl ammonium bromide (TBAB) (0.1 mmol), Ag2O (0.2 mmol), and Pd(PPh3)4 (0.01 mmol) in 1,4-dioxane/HOAc/DMSO (1.5 mL; v/v/v=7.5:1.5:1). The reaction mixture was stirred vigorously at 120 °C in an oil bath for 21 h. Then it was cooled to room temperature and diluted with ethyl acetate and filtered. After the filtrate was concentrated under reduced pressure, the residue was purified through the flash column chromatography on silica gel to afford the desired products.

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Rx-ID: 39366655

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90%

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With dipotassium peroxodisulfate; tetrakis(triphenylphosphine) palladium(0); silver carbonate in 1,4dioxane; acetic acid; N,N-dimethyl-formamide

T=120°C; 21 h; Hide Experimental Procedure

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Gong, Wei-Jie; Liu, De-Xian; Li, Fei-Long; Gao, Jun; Li, Hong-Xi; Lang, Jian-Ping

Tetrahedron, 2015 , vol. 71, # 8 p. 1269 - 1275 Title/Abstract Full Text View citing articles Show Details

16:(Furan-2-yl)(2-(pyridin-2-yl)benzo[b]thiophen-3-yl)methanone (3m)

4.2.16 Phenyl(2-(pyridin-2-yl)benzofuran-3-yl)methanone (5a) Yellow solid. Mp 146-147 °C. 1H NMR (400 MHz, CDCl3): δ=8.43-8.42 (m, 1H), 7.90 (d, J=8.0 Hz, 2H), 7.84 (d, J=8.0 Hz, 1H), 7.70-7.64 (m, 2H), 7.56-7.48 (m, 2H), 7.43-7.34 (m, 3H), 7.30-7.28 (m, 1H), 7.17-7.14 (m, 1H) ppm. 13C NMR (400 MHz, CDCl3): δ=192.4, 154.3, 153.2, 149.6,

147.9, 138.0, 136.7, 133.1, 129.6, 128.4, 128.2, 126.2, 124.0, 123.5, 122.2, 121.4, 118.6, 111.7 ppm. LC-MS (EI): m/z calcd [M+1]+=300.1; found: 300.1.

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Rx-ID: 39861846

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95%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

General procedure: An over-dried Schlenk tube was charged with tetrabutylammonium iodide (TBAI) (0.1 mmol),phenylglyoxylic acid (1a) (0.5 mmol) and cyclohexene (2a) (1.5 mmol) in benzene (2 mL) wasadded, Then tert-butyl hydroperoxide (1.25 mmol, 5~6 M in decane) was added dropwise into themixture at room temperature. The resulting mixture was stirred at 90 °C for 12 h. Then, the cooledreaction mixture was dissolved in water (5 mL) and extracted with CH2Cl2 (3×5 mL). Thecombined organic layer was dried with anhydrous MgSO4, and the product was further purified bysilica gel column chromatography and eluted with ethyl acetate and petroleum ether mixture toafford the product.

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Rx-ID: 41975315

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68%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

65%

With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

General procedure: A mixture of N-nitrosoaniline 1 (0.3 mmol), α-oxocarboxylic acid 2 (0.45 mmol), Pd(OAc)2 (0.03 mmol, 6.9 mg), K2S2O8 (0.6 mmol, 162.3 mg) in 1,4-dioxane/AcOH (7 : 3, 3 mL) was stirred at 80 °C for 12 h. The mixture was filtered by a silica gel plug with ethyl acetate as the eluent and evaporated in vacuum. The residual was separated on a silica gel column with petroleum ether/ethyl acetate as the eluent to give the desired product 3 as a mixture of inseparable syn and anti isomers.

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Rx-ID: 42810377

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93%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 0.833333 h; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 17; 22-23 ; Title/Abstract Full Text Show Details

1:Preparation of (Z)-3,7-dimethyl-2,6-octadienyl 2-oxo-2-phenylacetate

8.8.03-7.97 (m, 2H); 7.69-7.61 (m, 1H); 7.54-7.47 (m, 2H); 5.48 (dt, J=7.1, 1.1, 1H); 5.14-5.02 (m, 1H); 4.88 (dd, J=7.3, 1.0, 2H); 2.23-2.15 (m, 2H); 2.15-2.06 (m, 2H); 1.80 (s, 3H); 1.67 (s, 3H); 1.60 (s, 3H). (0184) 13C-NMR (90.6 MHz): δ 186.42 (s); 163.89 (s); 144.50 (s); 134.84 (d); 132.55 (s); 132.43 (s); 130.04 (d); 128.86 (d); 123.38 (d); 117.92 (d); 62.72 (t); 32.26 (t); 26.59 (t); 25.68 (q); 23.55 (q); 17.67 (q).

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Rx-ID: 42810379

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86%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 15 h; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 17; 19 ; Title/Abstract Full Text Show Details

1:Preparation of (+-)-2,6-dimethyl-5-heptenyl 2-oxo-2-phenylacetate

General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product. Preparation of (±)-2,6-dimethyl-5-heptenyl 2-oxo-2-phenylacetate (0137) As described above in the general method stirred at room temperature for 1.5 h. Column chromatography (SiO2, heptane/ether 4:1, then 1:1) gave 9.63 g (86percent) of a yellow oil. (0138) 1H-NMR (360 MHz): δ 8.03-7.97 (m, 2H); 7.69-7.63 (m, 1H); 7.55-7.48 (m, 2H); 5.13-5.05 (m, 1H); 4.29 (ABX, J=10.7, 5.9, 1H); 4.20 (ABX, J=10.7, 6.7, 1H); 2.12-1.90 (m, 3H); 168 (s, 3H); 1.60 (s, 3H); 1.55-1.42 (m, 1H); 1.32-1.18 (m, 1H); 1.01 (t, J=6.7, 3H). (0139) 13C-NMR (90.6 MHz): δ 186.53 (s); 164.14 (s); 134.88 (d); 132.53 (s); 131.92 (s); 130.00 (d); 128.92 (d); 124.00 (d); 70.91 (t); 33.23 (t); 32.14 (d); 25.72 (q); 25.21 (t); 17.68 (q); 16.73 (q).

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Rx-ID: 42810381

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91%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=20°C; 75.75 h; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 22 ; Title/Abstract Full Text Show Details

1:Preparation of ((6S,7S)-3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl 2-oxo-2-phenylacetate

General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product Preparation of ((6S,7S)-3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methyl 2-oxo-2-phenylacetate (0176) As described above in the general method with ((6S,7S)-3,5,5,6,7,8,8-heptamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)methanol (10.15 g, 39.0 mmol) and DCC in dichloromethane (20 ml) added during 45 min and stirred at room temperature for 75 h. Column chromatography (SiO2, heptane/ether 4:1) gave 8.09 g (91percent) of the product. (0177) 1H-NMR (360 MHz): δ 7.99-7.93 (m, 2H); 7.66-7.59 (m, 1H); 7.51-7.43 (m, 2H); 7.37 (s, 1H); 7.18 (s, 1H); 5.40 (s, 2H); 2.37 (s, 3H); 1.64-1.51 (m, 2H); 1.30 (s, 6H); 1.08 (s, 6H); 0.96 (d, J=6.3, 6H). (0178) 13C-NMR (90.6 MHz): δ 186.29 (s); 163.92 (s); 146.70 (s); 143.56 (s); 134.85 (d); 133.98 (s); 132.49 (s); 129.97 (d); 129.65 (s); 129.24 (d); 129.01 (d); 128.85 (d); 66.57 (t); 39.20 (d); 37.68 (s); 37.51 (s); 29.50 (q); 29.38 (q); 25.58 (q); 25.46 (q); 18.68 (q); 13.80 (q).

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Rx-ID: 43201293

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85%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

General procedure: In a 35 mL sealed tube, a solution of 3 mL of 1,4-dioxane, acyhydrazines 1 (0.5mmol), α-ketoacids 2 (0.5 mmol) , Na2CO3 (0.6 mmol), KI (0.05 mmol) and TBHP (2.0 mmol) was sequentially added. The reaction mixture was stirred at 120 °C for 5 h and then cooled to room temperature. Then, the mixture extracted with ethyl acetate (2 × 10 mL), and the organic layer was combined and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure, the residue was separated by flash column chromatography to afford the pure product 3 (PE:EA = 20:1).

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Rx-ID: 43201295

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90%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43201301

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91%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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88%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Reagent/catalystSolventTemperature; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43606860

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87%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

12:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

General procedure: The mixture of phenylglyoxylic acid (0.2mmol), propiophenone (0.2mmol), TBHP (0.4mmol), TBAI (0.04mmol) and ethyl acetate (2mL) was stirred at 80°C for 24h in a 15mL sealed tube successively. After cooling down, the reaction mixture was washed with Na2S2O3 solution, and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. After drying, the mixture was concentrated under vacuum, and the crude product was purified by column chromatography on silica gel with petroleum ether–ethyl acetate (50:1) as eluent.

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Rx-ID: 43606962

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88%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Reagent/catalystSolventTemperature; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

A typical procedure for the synthesis of α-acyloxycarbonyl compounds

(d, J=6.9Hz, 3H); 13C NMR (100MHz, CDCl3): δ 196.7, 165.9, 134.4, 133.5, 133.2, 129.8, 129.5, 128.7, 128.4, 128.3, 71.8, 17.1.

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Rx-ID: 9975402

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93%

With 4-(N,N-dimethlyamino)pyridine; diisopropyl-carbodiimide in dichloromethane

T=0 - 20°C;

Mizutani, Yusuke; Tanimoto, Hiroki; Morimoto, Tsumoru; Nishiyama, Yasuhiro; Kakiuchi, Kiyomi

Tetrahedron Letters, 2012 , vol. 53, # 44 p. 5903 - 5906,4 Title/Abstract Full Text Show Details

90%

With 4-(N,N-dimethlyamino)pyridine; dicyclohexyl-carbodiimide in toluene

T=20°C; Reflux;

Li, Shengkun; Xiao, Taifeng; Li, Dangdang; Zhang, Xumu

Organic Letters, 2015 , vol. 17, # 15 p. 3782 - 3785 Title/Abstract Full Text View citing articles Show Details

85%

in benzene

20 h; Heating;

Fennie, Michael W.; DiMauro, Erin F.; O'Brien, Erin M.; Annamalai, Venkatachalam; Kozlowski, Marisa C.

Tetrahedron, 2005 , vol. 61, # 26 p. 6249 - 6265 Title/Abstract Full Text View citing articles Show Details

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in benzene

Reflux;

Martin, Nolwenn J. A.; Cheng, Xu; List, Benjamin

Journal of the American Chemical Society, 2008 , vol. 130, # 42 p. 13862 - 13863 Title/Abstract Full Text View citing articles Show Details

in water; toluene

6 h; Reflux;

Endo, Kohei; Yakeishi, Sayuri; Takayama, Ryotaro; Shibata, Takanori

Chemistry - A European Journal, 2014 , vol. 20, # 29 p. 8893 - 8897 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994459

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91%

Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6acac)2; cyclohexylamine; copper(I) bromide in quinoline

T=100°C; 10 h; Inert atmosphereMolecular sieve; Stage #2: With hydrogenchloride in tetrahydrofuran; quinoline; water

T=80°C; 1 h; Inert atmosphere;

Collet, Florence; Song, Bingrui; Rudolphi, Felix; Goossen, Lukas J.

European Journal of Organic Chemistry, 2011 , # 32 p. 6486 - 6501 Title/Abstract Full Text View citing articles Show Details

57%

With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045

T=170°C; 16 h;

Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994472

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83%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994476

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82%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994482

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78%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 38846864

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83%

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With copper diacetate in acetonitrile

T=80°C; 16 h; Hide Experimental Procedure

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Park, Sujin; Jung, Youngeun; Kim, Ikyon

Tetrahedron, 2014 , vol. 70, # 41 p. 7534 - 7550 Title/Abstract Full Text View citing articles Show Details

1:Synthesis of 9

A mixture of 3a (30 mg, 0.15 mmol), phenylglyoxylic acid (3 equiv), and Cu(OAc)2 (1.2 equiv) in CH3CN (1 mL) was stirred at 80 °C for 16 h. After the reaction mixture was concentrated in vacuo, the residue was purified by silica gel column chromatography (hexanes/ethyl acetate/dichloromethane=30:1:2 to 10:1:2) to give 9 (37.1 mg, 83percent). A

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Rx-ID: 39180153

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A: 24% B: 68%

With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; Reagent/catalystSolvent; Hide Experimental Procedure

Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

General procedure: A 10mL oven-dried Schlenk-tube was charged with AgNO3 (3.4mg, 10molpercent), coumarin (1, 0.2mmol, 1.0equiv), and K2S2O8 (108mg, 0.4mmol, 2.0equiv). The tube was evacuated and backfilled with nitrogen (three times). α-Oxocarboxylic acids (2, 0.48mmol, 2.4equiv) in DMSO/H2O (1:1) 2mL were added by syringe. The tube was then sealed and the mixture was stirred for 24h at room temperature. Upon completion of the reaction, the mixture was diluted with EtOAc, filtered through a pad of Celite, and the filtrate was then removed under vacuo. The residue was purified with chromatography column on silica gel (gradient eluent of EtOAc/petroleum ether: 1:30 to 1:15) to give the corresponding products 3 or 4 in yields listed in Tables 2 and 3. 4.3.1. 3,4-Dibenzoyl-chromen-2-one (3a) A white solid, mp 147–149°C, Rf 0.2 (EtOAc/petroleum ether=1:10); 1H NMR (400MHz, CDCl3): δ=7.89–7.88 (d, J=7.2Hz, 2H), 7.82–7.80 (d, J=7.2Hz, 2H), 7.68–7.56 (m, 3H), 7.50–7.41 (m, 5H), 7.29–7.23 (m, 2H); 13C NMR (100MHz, CDCl3): δ=192.9, 191.4, 158.3, 154.1, 153.3, 136.0, 135.3, 135.0, 134.1, 133.7, 129.8, 129.4, 129.0, 128.6, 127.3, 125.2, 124.8, 117.4, 116.8ppm; IR (KBr): υmax 1727, 1668, 1598, 1249cm−1; HRMS (ESI) calcd for C23H14NaO4 [M+Na]+ 377.0784, found 377.0784.

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Rx-ID: 39180166

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56%

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

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Rx-ID: 39861843

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80%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

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Rx-ID: 39861844

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83%

With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

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Rx-ID: 39861845

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81%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

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Rx-ID: 39861849

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84%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Reagent/catalystTemperature; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

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Rx-ID: 40481586

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82%

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Stage #1: in 1,2-dichloro-ethane

T=150°C; 10 h; Microwave irradiation; Stage #2: With trifluoroacetic acid in 1,2-dichloro-ethane

T=100°C; 0.166667 h; Microwave irradiation; Hide Experimental Procedure

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Chen, Zhong-Zhu; Tang, Ying; Zuo, Lei; Tang, Dian-Yong; Zhang, Jin; Xu, Zhi-Gang

Synlett, 2014 , vol. 25, # 17 art. no. ST-2014-W0558-L, p. 2518 - 2520 Title/Abstract Full Text View citing articles Show Details

General Procedure for the Synthesis of Compound 14

General procedure: A solution of 2-(N-boc-amino)phenylisocyanide (0.50 mmol) and carboxylic acid (0.50 mmol) in DCE (2 mL) was subjected to microwave irradiation at 150 °C for 10 min. After the microwave vial was cooled to r.t., TFA (0.20 mL) was added to the mixture and treated in microwave again at 100 °C for 10 min. Then, the solvent was removed, and the residue was diluted with EtOAc (15 mL) and washed with sat. Na2CO3 (15 mL) and brine (10 mL). The organic layer was dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography using a gradient of EtOAc–hexane (10–80percent) to afford the relative benzimidazole products.

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Rx-ID: 40481591

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83%

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Stage #1: in 1,2-dichloro-ethane

T=150°C; 10 h; Microwave irradiation; Stage #2: With trifluoroacetic acid in 1,2-dichloro-ethane

T=100°C; 0.166667 h; Microwave irradiation; Hide Experimental Procedure

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Chen, Zhong-Zhu; Tang, Ying; Zuo, Lei; Tang, Dian-Yong; Zhang, Jin; Xu, Zhi-Gang

Synlett, 2014 , vol. 25, # 17 art. no. ST-2014-W0558-L, p. 2518 - 2520 Title/Abstract Full Text View citing articles Show Details

General Procedure for the Synthesis of Compound 14

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Rx-ID: 41975311

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94%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

62%

With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

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Rx-ID: 42810374

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83%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 22 h; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 20 ; Title/Abstract Full Text Show Details

1:Preparation of (+-)-3-(4-tert-butyl-1-cyclohexen-1-yl)propyl 2-oxo-2-phenylacetate

General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product. Preparation of (±)-3-(4-tert-butyl-1-cyclohexen-1-yl)propyl 2-oxo-2-phenylacetate (0153) As described above in the general method stirred at room temperature for 22 h. Column chromatography (SiO2, heptane/ether 9:1) gave 8.15 g (83percent) of a yellow oil. (0154) 1H-NMR (360 MHz): δ 8.04-7.97 (m, 2H); 7.69-7.62 (m, 1H); 7.55-7.47 (m, 2H); 5.47-5.41 (m, 1H); 4.37 (t, J=6.7, 2H); 2.12-1.68 (m, 9H); 1.33-1.07 (m, 2H); 0.86 (s, 9H). (0155) 13C-NMR (90.6 MHz): δ 186.46 (s); 164.00 (s); 135.80 (s); 134.89 (d); 132.49 (s); 130.02 (d); 128.89 (d); 122.27 (d); 66.03 (t); 44.11 (d); 33.48 (t); 32.18 (s); 29.62 (t); 27.23 (q); 26.79 (t); 26.37 (t); 24.21 (t).

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Rx-ID: 43201296

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76%

With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43201297

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83%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43201298

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81%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43201303

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80%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43378078

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78%

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With boron trifluoride diethyl etherate; toluene-4-sulfonic acid in chlorobenzene

T=70°C; 6 h; Hide Experimental Procedure

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Suzhou University; Zhu, Chen; Mao, Wenbin

Patent: CN105461671 A, 2016 ; Location in patent: Paragraph 0025; 0026; 0027; 0028 ; Title/Abstract Full Text Show Details

1:One embodiment of the reaction of benzoyl formic acid and phenylacetylene, synthesis of compound.

In a reaction tube was added benzoyl formic acid 0.3mmol, 0.9mmol phenylacetylene, 0.6mmol p-toluenesulfonic acid monohydrate, and 0.06 mmol of boron trifluoride etherate 2mL chlorobenzene, reaction at 70 degrees 6h, the reaction after the solvent was distilled off under reduced pressure, using petroleum ether: ethyl acetate, column chromatography, and the petroleum ether: ethyl acetate in a volume ratio of 10: 1 to give pure product in 78percent yield, 98percent pure.

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80%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

9:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

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Rx-ID: 43606836

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82%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

10:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

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Rx-ID: 43606850

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82%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

11:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

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Rx-ID: 43606884

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78%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

13:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

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Rx-ID: 43606917

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76%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

19:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

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Rx-ID: 44045684

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78%

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-Nmethylmethanaminium hexafluorophosphate in N,N-dimethyl-formamide

T=20°C; Hide Experimental Procedure

Shanghai De Novo Pharmatech Co., Ltd; Gao, Daxin

Patent: CN102952118 B, 2016 ; Location in patent: Paragraph 0259-0262 ; Title/Abstract Full Text Show Details

9:1-((1S,4S)-5-(2-fluro-5-((4-oxo-3,4,5,6,7,8-hexahydrophthalazin-1-yl)methyl)benzoyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl)-2-phenylethane-1,2-dione

The 4-(3-((1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carbonyl)-4-fluorobenzyl)-5,6,7,8-tetrahydrophthalazin-1(2Η)-one(20mg, 0.052mmol), 2-oxo-2-phenylacetic acid (9.42mg, 0.062mmol), DIPEA (13mg, 0.104mmol) and HATU (25mg, 0.067mmol) was dissolved in DMF (2ml), and the mixture was stirred overnight at room temperature until the reaction was complete (monitored by TLC). the mixture was washed with methylene chloride and water (50ml) separated, the organic phase was washed with water, 0.1N hydrochloric acid solution and saturated brine reaction , dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated to give a crude product, and then purified by TLC prep plate (DCM:MeOH = 20:1), to give the desired product (21mg, 78percent), as a white solid.

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Rx-ID: 44045696

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84.4%

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With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-Nmethylmethanaminium hexafluorophosphate in N,N-dimethyl-formamide

T=20°C; Hide Experimental Procedure

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Shanghai De Novo Pharmatech Co., Ltd; Gao, Daxin

Patent: CN102952118 B, 2016 ; Location in patent: Paragraph 0294-0297 ; Title/Abstract Full Text Show Details

14:1-(4-(2-fluor-5-((4-oxo-3,4,5,6,7,8-hexahydrophthalazin-1-yl)methyl)benzoyl)-1,4-diazepan-1-yl)-2-phenylethane-1,2-dione

4-(3-(1,4-diazepane-1-carbonyl)-4-fluorobenzyl)-5,6,7,8-tetrahydrophthalazin-1(2Η)-one (15mg , 0.039mmol), 2-oxo-2-phenylacetic acid (7mg, 0.047mmol), DIPEA (10.1mg, 0.078mmol) and HATU (19.3mg, 0.051mmol) was dissolved in DMF (1.5ml), and the mixture was stirred overnight at room temperature until the reaction was complete (monitored by TLC). The reaction mixture was diluted with dichloromethane and water (50ml) separated, the organic phase was washed with water, and washed with 0.1N hydrochloric acid and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered the filtrate was concentrated to give a crude product, and then purified by TLC prep plate (DCM:MeOH = 20:1), to give the desired product as a white solid (17mg, 84.4percent), it was.

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Rx-ID: 27994458

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97%

Stage #1: With 1,1'-bis-(diphenylphosphino)ferrocene; 1,10-phenanthroline; Pd(F6acac)2; cyclohexylamine; copper(I) bromide in quinoline

T=100°C; 10 h; Inert atmosphereMolecular sieve; Stage #2: With hydrogenchloride in tetrahydrofuran; quinoline; water

T=80°C; 1 h; Inert atmosphere;

Collet, Florence; Song, Bingrui; Rudolphi, Felix; Goossen, Lukas J.

European Journal of Organic Chemistry, 2011 , # 32 p. 6486 - 6501 Title/Abstract Full Text View citing articles Show Details

50%

With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994470

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73%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994471

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70%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 27994477

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67%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 28907907

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66%

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With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=0 - 20°C; Inert atmosphere; Hide Experimental Procedure

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Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark

Patent: US2009/312314 A1, 2009 ; Location in patent: Page/Page column 33-34 ; Title/Abstract Full Text Show Details

37.b.2:

To a solution of [2-(4-trifluoromethyl-phenyl)-ethyl]-(6-trifluoromethyl-pyridin-3-yl)-amine (50 mg) in CH2Cl2 (3 mL) was added under a nitrogen atmosphere at 0° C. benzoyl formic acid (1.1 eq., commercially available) and EDC (1.1 eq). After stirring for 12 h a ambient temperature, the mixture was washed with aqueous Na2CO3 (saturated, 2.5 mL) and water (2.5 mL), the combined aqueous layers were extracted with CH2Cl2 (3.x.2.5 mL) and the combined organic layers dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (46 mg, 66percent) as a light yellow solid. MS m/e: 467.2 [M+H]+.

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Rx-ID: 29056988

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67%

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Stage #1: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=0°C; 1 h; Inert atmosphere; Stage #2: With methanol; sodium tetrahydroborate

T=20°C; 3 h; Hide Experimental Procedure

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Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark

Patent: US2009/312314 A1, 2009 ; Location in patent: Page/Page column 15 ; Title/Abstract Full Text Show Details

2:(S)-N-(3,4-Dimethyl-phenyl)-2-hydroxy-2-phenyl-N-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-acetamide

To a solution of (3,4-dimethyl-phenyl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (800 mg, 0.27 mmol, prepared as described in example 1, step 3) in CH2Cl2 (3 mL) was added under a nitrogen atmosphere at 0° C. benzoylformic acid (61 mg, 0.41 mmol), EDC (130 mg, 0.68 mmol). After stirring for 1 h, the mixture was concentrated and redissolved in MeOH (3 mL) and treated with NaBH4 (206 mg, 5.44 mmol) and stirring continued for 3 h at ambient temperature. It was diluted with TBME (15 mL) and aqueous K2CO3 (2 M, 15 mL), stirred further for 20 min, the layers separated and the organic layer washed with water (15 mL). The combined aqueous layers were extracted with TBME (15 mL) and the combined organic layers dried over sodium sulfate. Concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the racemic compound (78 mg, 67percent) as a pale yellow oil. MS m/e: 429.2 [M+H]+ which was then separated by chiral HPLC to provide the title compound as an off white solid MS m/e: 429.2 [M+H]+.

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Rx-ID: 39861841

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67%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

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Rx-ID: 42810378

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68%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=20°C; 18 h; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 17; 21-22 ; Title/Abstract Full Text Show Details

1:Preparation of (+-)-1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethyl 2-oxo-2-phenylacetate

General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product. Preparation of (±)-1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethyl 2-oxo-2-phenylacetate (0173) As described above in the general method with (±)-1-(3,5,5,6,8,8-hexamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)ethanol (9.55 g, 36.7 mmol) in dichloromethane (50 ml) stirred at room temperature for 18 h. Repetitive column chromatography (SiO2, heptane/ether 4:1 and 95:5) gave 5.68 g (68percent) of a colourless oil. (0174) 1H-NMR (360 MHz): δ 7.96-7.89 (m, 2H); 7.66-7.58 (m, 1H); 7.46 (t, J=7.7, 2H); 7.35 (s, 1H); 7.14 (s, 1H); 6.32

(q, J=6.5, 1H); 2.39 (s, 3H); 1.92-1.79 (m, 1H); 1.72-1.56 (m, 4H); 1.40-1.17 (m, 10H); 1.06 (d, J=2.8, 3H); 0.98 (d, J=6.7, 3H). (0175) 13C-NMR (90.6 MHz): δ 186.60 (s); 163.48 (s); 145.97 (s); 142.87 (s); 135.63 (s); 134.79 (d); 132.50 (s); 131.92 (s); 131.87 (s); 129.99 (d); 128.97 (d); 128.85 (d); 123.49 (d); 123.39 (d); 72.14 (d); 43.67 (t); 37.50 (s); 34.53 (d); 34.17 (s); 32.43 (q); 32.14 (q); 32.03 (q); 28.53 (q); 24.99 (q); 24.92 (q); 21.34 (q); 18.86 (q); 16.82 (q).

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Rx-ID: 42810382

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66%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 24 h; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 18 ; Title/Abstract Full Text Show Details

1:Preparation of (Z)-3-nonenyl 2-oxo-2-phenylacetate

General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product. Preparation of (Z)-3-nonenyl 2-oxo-2-phenylacetate (0131) As described above in the general method with (Z)-3-nonenol (1.28 g, 9.0 mmol, 1.4 eq.) in dichloromethane (15 ml) and DCC in dichloromethane (7 ml) stirred at room temperature for 24 h. Column chromatography (SiO2, heptane/ethyl acetate 9:1) gave 1.21 g (66percent) of a slightly yellow oil. (0132) 1H-NMR (400 MHz): δ 8.04-7.98 (m, 2H); 7.69-7.62 (m, 1H); 7.54-7.47 (m, 2H); 5.61-5.51 (m, 1H); 5.44-5.34 (m, 1H); 4.39 (t, J=6.9, 2H); 2.58-2.50 (m, 2H); 2.08-2.00 (m, 2H); 1.39-1.20 (m, 6H); 0.86 (t, J=6.9, 3H). (0133) 13C-NMR (100.6 MHz): δ 186.34 (s); 163.87 (s); 134.88 (d); 133.85 (d); 132.49 (s); 130.06 (d); 128.87 (d); 123.38 (d); 65.62 (t); 31.45 (t); 29.19 (t); 27.32 (t); 26.74 (t); 22.53 (t); 14.02 (q).

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Rx-ID: 42810383

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67%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; Hide Experimental Procedure

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Firmenich SA; Berthier, Damien; Herrmann, Andreas; Paret, Nicolas; Ouali, Lahoussine

Patent: US9334464 B2, 2016 ; Location in patent: Page/Page column 17; 19 ; Title/Abstract Full Text Show Details

1:Preparation of decyl 2-oxo-2-phenylacetate

General Method for the Preparation of 2-Oxo-2-Phenylacetates (0115) A solution of benzoylformic acid (1 eq.), 4-(dimethylamino)pyridine (DMAP, 0.1 eq.) and the alcohol corresponding to the aldehyde or ketone to be released (10.00 g, ca. 1.7 eq.) in dichloromethane (50100 ml) was cooled on an ice-bath before a solution of N,N′-dicyclohexylcarbodiimide (DCC, ca. 1.2 eq.) in dichloromethane (40 ml) was added dropwise during 15-30 min. The reaction mixture was stirred for 10 min at 0° C., then at room temperature for 3-6 h. The precipitate formed in the reaction was filtered off and the filtrate taken up in ether, washed with water (3×), HCl (10percent, 3×) and a saturated solution of NaHCO3 (3×). The organic layer was dried (Na2SO4) and concentrated to give the crude reaction product. Preparation of decyl 2-oxo-2-phenylacetate As described above in the general method with decanol (32.50 g, 205.3 mmol) in dichloromethane (350 ml) and DCC in dichloromethane (150 ml) stirred at room temperature overnight. Kugelrohr distillation (to remove remaining decanol) and repetitive column chromatography (SiO2, heptane/ethyl acetate 7:3) gave 23.41 g (67percent) of a slightly yellow oil. 1H-NMR (400 MHz): δ 8.03-7.98 (m, 2H); 7.69-7.63 (m, 1H); 7.54-7.48 (m, 2H); 4.39 (t, J=6.8, 2H); 1.82-1.73 (m, 2H); 1.47-1.19 (m, 14H); 0.88 (t, J=6.9, 3H). 13C-NMR (100.6 MHz): δ 186.50 (s); 164.02 (s); 134.87 (d); 132.55 (s); 130.02 (d); 128.89 (d); 66.41 (t); 31.88 (t); 29.50 (t); 29.47 (t); 29.29 (t); 29.17 (t); 28.48 (t); 25.80 (t); 22.67 (t); 14.11 (q).

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Rx-ID: 43201300

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71%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43201306

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65%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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73%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

15:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

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Rx-ID: 43606900

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67%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

16:A typical procedure for the synthesis of α-acyloxycarbonyl compounds

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Rx-ID: 43606905

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70%

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With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h; Sealed tube; Hide Experimental Procedure

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Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

17:1-(2-Fluorophenyl)-1-oxopropan-2-yl benzoate (4g)

The mixture of phenylglyoxylic acid (0.2mmol), propiophenone (0.2mmol), TBHP (0.4mmol), TBAI (0.04mmol) and ethyl acetate (2mL) was stirred at 80°C for 24h in a 15mL sealed tube successively. After cooling down, the reaction mixture was washed with Na2S2O3 solution, and extracted by ethyl acetate for three times. The obtained top organic layer was dried with anhydrous MgSO4. After drying, the mixture was concentrated under vacuum, and the crude product was purified by column chromatography on silica gel with petroleum ether–ethyl acetate (50:1) as eluent.

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Rx-ID: 27994481

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59%

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With quinoline; 1,10-phenanthroline; tris-(o-tolyl)phosphine; copper(I) bromide in 1-methyl-pyrrolidin-2one; quinoline

T=170°C; 16 h;

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Goossen, Lukas J.; Rudolphi, Felix; Oppel, Christoph; Rodriguez, Nuria

Angewandte Chemie - International Edition, 2008 , vol. 47, # 16 p. 3043 - 3045 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 33998720

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56%

Stage #1: in water; dimethyl sulfoxide

T=100°C; 1 h; Inert atmosphere; Stage #2: With dipotassium peroxodisulfate

3 h; Inert atmosphere;

Yang, Zhiyong; Chen, Xiang; Wang, Sizhuo; Liu, Jidan; Xie, Kai; Wang, Anwei; Tan, Ze

Journal of Organic Chemistry, 2012 , vol. 77, # 16 p. 7086 - 7091 Title/Abstract Full Text View citing articles Show Details

41%

With copper(l) iodide; tetrafluoroboric acid in water; dimethyl sulfoxide

T=130°C; 9 h; Inert atmosphereSealed tube; chemoselective reaction;

Feng, Qiang; Song, Qiuling

Advanced Synthesis and Catalysis, 2014 , vol. 356, # 11-12 p. 2445 - 2452 Title/Abstract Full Text View citing articles Show Details

15%

With dipotassium peroxodisulfate; FeCl3·6H2O in water; dimethyl sulfoxide

T=100°C; 12 h; Hide Experimental Procedure

Wang, Jian; Zhang, Xiao-Zhuan; Chen, Shan-Yong; Yu, Xiao-Qi

Tetrahedron, 2014 , vol. 70, # 2 p. 245 - 250 Title/Abstract Full Text View citing articles Show Details

3a_2

A dried reflux tube equipped witha magnetic stir bar charged with benzothiazole derivative (0.5 mmol 1.0equiv), benzylalcohol derivative (1.5mmol 3.0equiv), FeCl3·6H2O (0.1equiv), K2S2O8 (2.0 equiv), DMSO/H2O (2:1 mL) and the reaction vessel was placedin a 100°C oil bath for 12 h under air. After cooling to room temperature,the mixture was diluted with ethyl acetate and directly filtered through a padof celite and washed with water. The organic phase was dried over NaSO4and removed under reduced vacuum. The residue was purified by columnchromatography eluting with ethyl acetate and hexane to afford the desired product. A

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With 5 wt ruthenium/carbon; hydrogen in methanol

T=60°C; P=30003 Torr; 120 h; AutoclaveInert atmosphere; Optical yield = 14percent ee; Hide Experimental Procedure

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Wagner, Valentin; Schulz, Peter S.; Wasserscheid, Peter

Journal of Molecular Liquids, 2014 , vol. 192, p. 177 - 184 Title/Abstract Full Text View citing articles Show Details

Heterogeneously catalyzed hydrogenation reactions

The ionic liquid was dissolved in the respective solvent and rutheniumon activated charcoal was added (5percent Ru/C, 10 wt.percent with respect tothe substrate IL). The mixture was hydrogenated in a batch autoclaveat 60 °C, 40 bar hydrogen pressure for 5 days. After filtration of thecatalyst and removal of the solvent the product was obtained

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Rx-ID: 38887382

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94%

With Potassium peroxomonosulfate

T=65°C; 30 h; Hide Experimental Procedure

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Padala, Anil K.; Saikam, Varma; Ali, Asif; Ahmed, Qazi Naveed

Tetrahedron, 2015 , vol. 71, # 50 p. 9388 - 9395 Title/Abstract Full Text View citing articles Show Details

4.3 General procedure for preparation of esters (RCO2R′) 5 from 2-oxoacids (RCOCO2H) 3/2-oxoaldehydes (RCOCHO) 3 &/2-oxoesters (RCOCO2R″) 4

General procedure: A mixture of 2-oxoacids 2/2-oxoaldehydes 3/2-oxoesters 4 (0.5mmol), oxone (1.25mmol) and alcohol (1.5mL) in round bottomed flask was stirred at 65°C. After completion of the reaction that was confirmed by thin layer chromatography, the crude mixture was cooled to room temperature, filtered and purified by column chromatography using silica gel (100–200 ) with ethyl acetate and hexane as an eluent to afford the desired product 5 in 70–99 percent yields.

18%

With pyridine; chlorobenzene; copper(I) bromide

T=130°C; 24 h;

Huang, Xiaoqiang; Li, Xinyao; Zou, Miancheng; Song, Song; Tang, Conghui; Yuan, Yizhi; Jiao, Ning

Journal of the American Chemical Society, 2014 , vol. 136, # 42 p. 14858 - 14865 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 39180162

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43%

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

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Rx-ID: 39180163

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38%

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

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Rx-ID: 39180165

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36%

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

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Rx-ID: 39861842

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55%

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With tert -butyl hydrogen peroxide; tetra-(n-butyl)ammonium iodide in decane; benzene

T=20 - 90°C; 12 h; Schlenk technique; Hide Experimental Procedure

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Mo, Hanjie; Chen, Dingben; Xu, Lingzhen; Chen, Di; Pan, Fuyou; Yang, Jianguo

Synthesis (Germany), 2015 , vol. 47, # 2 p. 209 - 215 Title/Abstract Full Text View citing articles Show Details

(B) Typical experimental procedureGeneral experimental procedures for the TBAI-catalyzed synthesis ofcyclohex-2-enyl benzoate

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Rx-ID: 40545888

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65%

Stage #1: in methanol

T=50°C; Stage #2: With ammonium acetate in acetic acid

T=150°C; 0.166667 h; Microwave irradiation; Hide Experimental Procedure

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Zhang, Xiaoyan; Song, Guiting; Cui, Hailei; Xu, Zhigang; Zhu, Jin; Chen, Zhongzhu

Science China Chemistry, 2015 , vol. 58, # 7 p. 1239 - 1242 Title/Abstract Full Text View citing articles Show Details

2 Experimental

General procedure: General procedures for compounds 10 and 15 are as follows:a solution of aldehyde (0.50 mmol) and amine (0.50 mmol)in MeOH (1 mL) was stirred at room temperature for 10min in a 5 mL microwave vial. Next, acid (0.50 mmol) andisonitrile (0.50 mmol) were added separately. The mixturewas stirred at room temperature overnight. The reaction wasmonitored by TLC and the solvent was removed under nitrogenblowing. The residue was dissolved in AcOH (3 mL)and NH4AcO (2.5 mmol, 193 mg) was added and thentreated in microwave (MW) at 150 °C for 10 min. The solventwas removed under reduced pressure and the residuewas diluted with EtOAc (15 mL) and washed with sat. sodiumcarbonate and brine. The organic layer was dried overMgSO4 and concentrated. The residue was purified by silicagel column chromatography using a gradient of ethylacetate/hexane (1percent–100percent) to afford the relative products 9and 14a–14h.

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Rx-ID: 41406490

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96%

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With oxone

T=65°C; 30 h; Hide Experimental Procedure

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Padala, Anil K.; Saikam, Varma; Ali, Asif; Ahmed, Qazi Naveed

Tetrahedron, 2015 , vol. 71, # 50 p. 9388 - 9395 Title/Abstract Full Text View citing articles Show Details

4.3 General procedure for preparation of esters (RCO2R′) 5 from 2-oxoacids (RCOCO2H) 3/2-oxoaldehydes (RCOCHO) 3 &/2-oxoesters (RCOCO2R″) 4

56%

With copper(II) choride dihydrate; oxygen; lithium bromide

T=130°C; P=7500.75 Torr; 2 h; AutoclaveGreen chemistry;

Ma, Ran; He, Liang-Nian; Liu, An-Hua; Song, Qing-Wen

Chemical Communications, 2016 , vol. 52, # 10 p. 2145 - 2148 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 41997681

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14%

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With oxygen; copper(I) bromide in dimethyl sulfoxide

T=80°C; P=760.051 Torr; 24 h; Sealed tube; Hide Experimental Procedure

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Cheng, Hanchao; Bolm, Carsten

Synlett, 2016 , vol. 27, # 5 p. 769 - 772 Title/Abstract Full Text View citing articles Show Details

Typical Experimental Procedure

General procedure: A sealed tube (60 mL) wascharged with acetophenone (1a, 300 mg, 2.5 mmol), sulfoximine2a (77.6 mg, 0.5 mmol) and CuBr (14.3 mg, 0.1 mmol, 20molpercent), followed by the addition of DMSO (0.5 mL). The tube wasflushed with dioxygen for 1 min and then sealed with a pressurecap. The reaction mixture was vigorously stirred at 80 °Cfor 24 h. After cooling to ambient temperature, the product waspurified by column chromatography using hexane–EtOAc(10:1–2:1) as eluent to give product 3aa.

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Rx-ID: 42141601

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55%

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With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

2) General Procedures

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Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

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Rx-ID: 42141602

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56%

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With dipotassium peroxodisulfate; palladium diacetate in 1,4-dioxane; acetic acid

T=80°C; 12 h; regioselective reaction; Hide Experimental Procedure

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Yao, Jia-Ping; Wang, Guan-Wu

Tetrahedron Letters, 2016 , vol. 57, # 15 p. 1687 - 1690 Title/Abstract Full Text View citing articles Show Details

2) General Procedures

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Rx-ID: 43201294

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59%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures

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Rx-ID: 43201299

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55%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details

2.Experimental Procedures General procedure: In a 35 mL sealed tube, a solution of 3 mL of 1,4-dioxane, acyhydrazines 1 (0.5mmol), α-ketoacids 2 (0.5 mmol) , Na2CO3 (0.6 mmol), KI (0.05 mmol) and TBHP (2.0 mmol) was sequentially added. The reaction mixture was stirred at 120 °C for 5 h and then cooled to room temperature. Then, the mixture extracted with ethyl acetate (2 × 10 mL), and the organic layer was combined and dried with anhydrous Na2SO4. After removal of the solvent under reduced pressure, the residue was separated by flash column chromatography to afford the pure product 3 (PE:EA = 20:1).

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Rx-ID: 43201305

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55%

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With tert.-butylhydroperoxide; sodium carbonate; potassium iodide in 1,4-dioxane

T=120°C; 5 h; Sealed tube; Hide Experimental Procedure

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Gao, Peng; Wang, Juan; Bai, Zijing; Cheng, Hualei; Xiao, Jian; Lai, Mengnan; Yang, Desuo; Fan, Mingjin

Tetrahedron Letters, 2016 , vol. 57, # 41 p. 4616 - 4619 Title/Abstract Full Text Show Details