15_page_Benzaldehyde_to_propenylbenzene by Asch

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O ARY

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276 reactions in Reaxys

2017-11-15 01h:46m:17s (EST)

Search as: As drawn, No salts, No mixtures

1/88

2017-11-15 01:47:24

Rx-ID: 5150310 View in Reaxys 1/276 Yield 61 %

Conditions & References With boron trifluoride diethyl etherate in hexane, Time= 1h, Heating Kabalka, George W.; Li, Nan-Sheng; Tejedor, David; Malladi, Rama R.; Trotman, Sarah; Journal of Organic Chemistry; vol. 64; nb. 9; (1999); p. 3157 - 3161 View in Reaxys

58 %

1 :Preparation Example 1: Synthesis of l-(2-chlorophenyl)-trans-l-propene48ml of 2-chlorobenzenaldehyde (0.42mol) and 49.7ml of 3-pentanone (0.47mol) were dissolved in 600mL of hexane in flask, and then stirred with raising the temperature. 53.6ml of Boron trifluoride etherate (BF3OEt2, 0.42mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with IM sodium hydroxide solution (IM NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgS04) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38g, yield 58percent).1H NMR(400MHz, CDC13) 51.94(d, J=4.8Hz, 3H), 6.24(m, 1H), 6.78(d, J=14Hz, 1H), 7.11~7.51(m, 4H Stage 1: With boron trifluoride diethyl etherate in hexane, Reflux Stage 2: With sodium hydroxide in hexane, water Patent; BIO-PHARM SOLUTIONS CO., LTD.; CHOI, Yong Moon; WO2012/2773; (2012); (A2) English View in Reaxys

58 %

1 :Preparation Example 1 Synthesis of 1-(2-chlorophenyl)-trans-1-propene 48 ml of 2-chlorobenzenaldehyde (0.42 mol) and 49.7 ml of 3-pentanone (0.47mol) were dissolved in 600 mL of hexane in flask, and then stirred with raising the temperature. 53.6 ml of Boron trifluoride etherate (BF 3OEt2, 0.42 mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with 1M sodium hydroxide solution (1M NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38 g, yield 58percent). 1H NMR(400 MHz, CDCl ) δ1.94(d, J=4.8 Hz, 3H), 6.24(m, 1H), 6.78(d, J=14 Hz, 1H), 7.11~7.51(m, 4H) 3 With boron trifluoride diethyl etherate in hexane, Reflux Patent; Bio-Pharm Solutions Co., Ltd.; US2012/184762; (2012); (A1) English View in Reaxys

58 %

1 : Synthesis of 1-(2-chlorophenyl)-trans-1-propene Preparation Example 1 Synthesis of 1-(2-chlorophenyl)-trans-1-propene 48 ml of 2-chlorobenzenaldehyde (0.42 mol) and 49.7 ml of 3-pentanone (0.47 mol) were dissolved in 600 mL of hexane in flask, and then stirred with raising the temperature. 53.6 ml of Boron trifluoride etherate (BF 3OEt2, 0.42 mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with 1M sodium hydroxide solution (1M NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38 g, yield 58percent). 1H NMR (400 MHz, CDCl ) δ1.94 (d, J=4.8 Hz, 3H), 6.24 (m, 1H), 6.78 (d, J=14 Hz, 1H), 7.11~7.51 (m, 4H) 3 With boron trifluoride diethyl etherate in hexane, Reflux

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Patent; Bio-Pharm Solutions Co., Ltd.; US2013/5801; (2013); (A1) English View in Reaxys 58 %

1 : Synthesis of 1-(2-chlorophenyl)-trans-1-propene Preparation Example 1 Synthesis of 1-(2-chlorophenyl)-trans-1-propene 48 ml of 2-chlorobenzenaldehyde (0.42 mol) and 49.7 ml of 3-pentanone (0.47 mol) were dissolved in 600 mL of hexane in flask, and then stirred with raising the temperature. 53.6 ml of Boron trifluoride etherate (BF 3OEt2, 0.42 mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with 1M sodium hydroxide solution (1M NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgSO4) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38 g, yield 58percent). 1H NMR (400 MHz, CDCl ) δ1.94 (d, J=4.8 Hz, 3H), 6.24 (m, 1H), 6.78 (d, J=14 Hz, 1H), 7.11˜7.51 (m, 4H) 3 With boron trifluoride diethyl etherate in hexane, Reflux Patent; Bio-Pharm Solutions Co., Ltd.; Choi, Yong Moon; US2013/165408; (2013); (A1) English View in Reaxys

58 %

Preparation Example 1: Synthesis of l-(2-chorophenyl)-trans-l-propene 48ml of 2-chlorobenzenaldehyde (0.42mol) and 49.7ml of 3-pentanone (0.47mol) were dissolved in 600mL of hexane in flask, and then stirred with raising the temperature. 53.6ml of Boron trifluoride etherate (BF 3OEt2, 0.42mol) was added to the resultant under reflux conditions. When the reaction was completed, water was added thereto. After layer separation, the obtained organic layer was washed twice with IM sodium hydroxide solution (IM NaOH), and then the separated organic layer was washed with water. The separated organic layer was dehydrated with anhydrous magnesium sulfate (MgSC^) and concentrated. The concentrated residue was purified by a silica gel column chromatography to produce the title compound (38g, yield 58percent). NMR(400MHz, CDC13) 81.94(d, J=4.8Hz, 3H), 6.24(m, 1H), 6.78(d, J=14Hz, 1H), 7.1 1-7.5 l(m, 4H) With boron trifluoride diethyl etherate in hexane, Reflux Patent; BIO-PHARM SOLUTIONS CO., LTD.; CHOI, Yong Moon; WO2014/142477; (2014); (A1) English View in Reaxys

58 %

1 With boron trifluoride diethyl etherate in hexane, T= 65 °C Patent; BIO-PHARM SOLUTIONS CO., LTD.; CHOI, Yong Moon; (149 pag.); WO2017/150903; (2017); (A1) English View in Reaxys

O O

Rx-ID: 37716224 View in Reaxys 2/276 Yield 49 %

Conditions & References 2 : Example 2: (£ -l-Methoxy-4-(prop-l-en-l-yl) benzene ( 1-a) Example 1: Preparation of (E)-5-(hex-l-en-l-yl)-l,2,3-trimethoxybenzene: (1-g) To a mixture of 3,4,5-trimethoxybenzaldehyde (0.784 g, 0.004 mol), hexanal (0.5 g, 0.005 mol) and malononitrile (0.66 g, 0.01 mol), was added 30 ml of acetonitrile followed by the addition of glacial acetic acid (0.42 ml 0.0075 mol). The reaction mixture was stirred for 10 min and then ammonium acetate (0.385 g, 0.005 mol) was added. The reaction was stirred at 80 °C for 8 h. The mixture was then allowed to come to room temperature, filtered through Whatmann filter paper and the filtrate was concentrated on rotavapor. The residual oil was then partitioned between water and ethyl acetate and the organic extract was dried over sodium sulfate, concentrated and purified over silica gel using ethyl acetate - pet ether (3percent ethyl acetate in pet ether) as an eluent to give (E)-5-(hex-l-en-l- yl)-l,2,3-trimethoxybenzene as a colourless liquid (0.6 g, 60percent); IR (chloroform): 810, 925, 1377, 1506, 1582, 1651, 2929, 2989 cm- 1. 1H NMR (200 MHz, CDC13) : δ 0.93 (t, J - 7Hz, 3H), 1.30-1.56 (m, 4H), 2.27 (q, J = 7Hz, 2H), 3.84 (s, 3H), 3.88 (s, 6H), 6.14 (dt, J = 16, 7 Ηζ,ΙΗ), 6.32 (d, J = 16 Hz, 1H), 6.58 (s, 2H); l3C NMR (50 MHz, CDC13): δ 13.7, 22.0, 31.3, 32.4, 55.7 (2C), 60.6,

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102.6 (2C), 129.4, 130.5, 133.5, 136.9, 153.0 (2C); HRMS (ESI) m/z calcd for [C 15H2203 + Na]+: 273.1461, found 273.1462; [Ci5H2203 + H]+: 251.1642, found 251.1642. This compound was prepared from anisaldehyde and propionaldehyde following the procedure similar to the one described in Example 1. Colorless liquid; Yield: 49 percent; IR (Neat): 1036, 1 175, 1282, 1509, 1608, 2835, 2957, 3023 cm"1. 1H NMR (200 MHz, CDC13) : δ 1.89 (d, J = 6 Hz, 3H), 3.82 (s, 3H), 6.12 (dq, J = 16, 6 Hz, 1H), 6.38 (d, J = 16 Hz, 1H), 6.86 (d, J = 8 Hz, 2H), 7.29 (d, J = 8 Hz, 2H); NMR (50 MHz, CDC13): δ 18.3, 55.0, 1 13.7 (2C), 123.2, 126.7 (2C), 130.2, 130.6, 158.4.

I3C

With ammonium acetate, acetic acid, malononitrile in acetonitrile, Time= 8h, T= 80 °C , Reagent/catalyst, Solvent, Temperature, Wavelength Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; BORATE, Hanumant, Bapurao; GAIKWAD, Supriya, Hanumant; KUDALE, Ananda, Shahaji; CHAVAN, Subhash, Prataprao; PHARANDE, Shrikant, Ganpat; WAGH, Vitthal, Dattatraya; SAWANT, Vikram, Shahaji; WO2014/73003; (2014); (A1) English View in Reaxys I

I O

Rx-ID: 3556938 View in Reaxys 3/276 Yield

Conditions & References

97 %

With chromium dichloride in tetrahydrofuran, Time= 10h, T= 25 °C , var. reag.: CrCl 3, Zn, 5 h Okazoe, Takashi; Takai, Kazuhiko; Utimoto, Kiitiro; Journal of the American Chemical Society; vol. 109; nb. 3; (1987); p. 951 - 953 View in Reaxys

ortho-isopropoxy salicylaldehyde O

Rx-ID: 23912816 View in Reaxys 4/276 Yield

Conditions & References

95%

3 : Alternative Synthesis of ortho-Isopropoxy beta-Methyl Styrene [2]: Synthesis of ortho-Isopropoxy Salicylaldehyde [3] Similar to the procecure of Example 2, 6.5 g (53.2 mmol) of salicylaldehyde, 100 mL of anhydrous DMF, 6.5 g of K2CO3, and 10 g of isopropyl bromide (81.3 mmol) were added to a dry 250 mL round-bottom flask containing a magnetic stirbar. The heterogeneous mixture was stirred with heating to 60° C. for 24 hours when GC analysis indicated complete conversion to o-isopropoxy salicylaldehyde. Water 100 mL was added and the organics were washed with 2*100 mL of TBME, the TBME phases were combined and washed with 2*50 mL water, dried with anhydrous sodium sulfate, filtered and concentrated to yield [3] (8.3 g, 95percent yield). Salicylaldehyde Rt 6.473 minutes, ortho-isopropoxy salicylaldehyde Rt 10.648 minutes. 1H NMR (300 Mz) CDCl3 δ: 10.46 (CO), 7.8 (d, 1H aromatic), 7.5 (m, 1H, aromatic), 6.90 (t, 2H, aromatic), 4.64 (m, 1H, C(CH 3)2), 1.35 (J 6.3 Hz, 6H, CH(C3)2). With potassium carbonate in N,N-dimethyl-formamide Patent; Pederson, Richard L.; Woertink, Jason K.; Haar, Christopher M.; Gindelberger, David E.; Schrodi, Yann; US2003/166955; (2003); (A1) English View in Reaxys

O E

O O O

O O

Rx-ID: 37716226 View in Reaxys 5/276

4/88

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Yield

Conditions & References

33 %

7 : Example 7: (E)-l,2,3-Trimethoxy-5-(prop-l-en-l-yl) benzene (1-f) To a mixture of 3,4,5-trimethoxybenzaldehyde (0.784 g, 0.004 mol), hexanal (0.5 g, 0.005 mol) and malononitrile (0.66 g, 0.01 mol), was added 30 ml of acetonitrile followed by the addition of glacial acetic acid (0.42 ml 0.0075 mol). The reaction mixture was stirred for 10 min and then ammonium acetate (0.385 g, 0.005 mol) was added. The reaction was stirred at 80 °C for 8 h. The mixture was then allowed to come to room temperature, filtered through Whatmann filter paper and the filtrate was concentrated on rotavapor. The residual oil was then partitioned between water and ethyl acetate and the organic extract was dried over sodium sulfate, concentrated and purified over silica gel using ethyl acetate - pet ether (3percent ethyl acetate in pet ether) as an eluent to give (E)-5-(hex-l-en-l- yl)-l,2,3trimethoxybenzene as a colourless liquid (0.6 g, 60percent); IR (chloroform): 810, 925, 1377, 1506, 1582, 1651, 2929, 2989 cm-1. 1H NMR (200 MHz, CDC13) : δ 0.93 (t, J - 7Hz, 3H), 1.30-1.56 (m, 4H), 2.27 (q, J = 7Hz, 2H), 3.84 (s, 3H), 3.88 (s, 6H), 6.14 (dt, J = 16, 7 Ηζ,ΙΗ), 6.32 (d, J = 16 Hz, 1H), 6.58 (s, 2H); l3C NMR (50 MHz, CDC13): δ 13.7, 22.0, 31.3, 32.4, 55.7 (2C), 60.6, 102.6 (2C), 129.4, 130.5, 133.5, 136.9, 153.0 (2C); HRMS (ESI) m/z calcd for [C15H2203 + Na]+: 273.1461, found 273.1462; [Ci5H2203 + H]+: 251.1642, found 251.1642. This compound was prepared from 3,4,5-trimethoxybenzaldehyde and propionaldehyde following the procedure similar to the one described in Example 1. Colorless liquid; Yield: 33percent; IR (neat): 1010, 1126, 1238, 1273, 1506, 1582 1692, 2838, 2938 cm'1. 1H NMR (200 MHz, CDC13) : δ 1.87 (d, J= 6 Hz, 3H), 3.83 (s, 3H), 3.86 (s, 6H), 6.13 (dq, J = 16, 6 Ηζ,ΙΗ), 6.33 (d, J = 16 Hz, 1H), 6.55 (s, 2H). 13C NMR (50 MHz, CDCI3): δ 18.0, 55.6 (2C), 60.5, 102.4 (2C), 124.8, 130.6, 133.4, 136.7, 152.9 (2C). With ammonium acetate, acetic acid, malononitrile in acetonitrile, Time= 8h, T= 80 °C , Reagent/catalyst, Temperature Patent; COUNCIL OF SCIENTIFIC and INDUSTRIAL RESEARCH; BORATE, Hanumant, Bapurao; GAIKWAD, Supriya, Hanumant; KUDALE, Ananda, Shahaji; CHAVAN, Subhash, Prataprao; PHARANDE, Shrikant, Ganpat; WAGH, Vitthal, Dattatraya; SAWANT, Vikram, Shahaji; WO2014/73003; (2014); (A1) English View in Reaxys

N O N

Cl N

N N

Cl N O

Rx-ID: 44361273 View in Reaxys 6/276 Yield 14 %

Conditions & References 30.1 : Example 30: Preparation of Compound 69Step 1 To a solution of Compound 39 (28mg, 0.069mmol) in acetonitrile (1mL) was added propionaldehyde (12uL, 0.173mmol), malononitrile (22.8mg, 0.346mmol) and acetic acid (16uL, 0.277mmol), the solution was stirred at roomtemperature for 10 minutes. To the reaction mixture was added ammonium acetate (13.3mg, 0.173mmol), the solutionwas stirred at 80°C for 8 hours. To the reaction mixture was added water, and extracted with ethyl acetate. The organiclayer was dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue wad purified bysilica gel chromatography (ethyl acetate / hexane), and purified by suspension with ethyl acetate / hexane to yieldCompound 69 (4 mg, yield: 14percent) as a white solid.LC/MS Method: B, LC-MS: m/z=417. [M+H]+, retention time: 1.55min1H-NMR (CDCl3) δ: 7.69 (2H, d, J = 8.3 Hz), 7.48-7.45 (3H, m), 7.37-7.34 (2H, m), 7.08 (1H, d, J = 8.0 Hz), 4.87-4.81(4H, m), 4.56-4.55 (1H, m), 4.47 (1H, br s), 3.80-3.71 (2H, m), 3.51-3.48 (1H, m), 2.19-2.18 (1H, m), 1.57 (4H, dd, J =6.5, 2.7 Hz), 1.04-0.96 (3H, m). Stage 1: With acetic acid, malononitrile in acetonitrile, Time= 0.166667h, T= 20 °C Stage 2: With ammonium acetate in acetonitrile, Time= 8h, T= 80 °C Patent; The University of Tokyo; Tohoku University; Shionogi and Co., Ltd.; NAGANO, Tetsuo; OKABE, Takayoshi; KOJIMA, Hirotatsu; KAWAGUCHI, Mitsuyasu; NUREKI, Osamu; ISHITANI, Ryuichiro; NISHIMASU, Hiroshi; AOKI, Junken; FUJIKOSHI, Chiaki; KATOU, Manabu; ODAN, Masahide; TANAKA, Nobuyuki; TATENO, Yusuke; YAMANE, Junji; (144 pag.); EP3112369; (2017); (A1) English View in Reaxys

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Rx-ID: 24790905 View in Reaxys 7/276 Yield

Conditions & References 11 :To a mixture of dimethyl sulfoxide (70 mL) and tetrahydrofuran (200 mL) was added sodium hydride (60percent, oil, 1.29 g) at room temperature. After stirring at 50 DEG C for 1.5 hrs., the reaction mixture was cooled to room temperature. Thereto was added ethyl triphenyl phosphonium bromide (9.76 g) and the mixture was stirred at room temperature for 30 min. To this mixture was dropwise added further a solution (10 mL) of 2-benzyloxy-4-methoxymethoxybenzaldehyde (5.50 g) in dimethyl sulfoxide. The mixture was heated under reflux for 1 hr. Water was added to the reaction mixture, and the mixture was neutralized by adding 1N hydrochloric acid (33 mL) and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give an oil (4.94 g) from a fraction eluted with ethyl acetate-hexane (1:9, v/v). A mixture of this oil, 5percent palladium carbon (10.0 g) and tetrahydrofuran (300 mL) was subjected to catalytic hydrogenation at room temperature and 1 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2-hydroxy-4-methoxymethoxy-1-propylbenzene as a colorless oil (3.3 g, 83percent) from a fraction eluted with ethyl acetate-hexane (1:6, v/v). <1>H-NMR (CDCl3) delta : 0.96 (3H, t, J=7.2 Hz), 1.51-1.66 (2H, m), 2.51 (2H, t, J=7.6 Hz), 3.47 (3H, s), 4.76 (1H, s), 5.13 (2H, s), 6.50-6.59 (2H, m), 7.00 (1H, d, J=8.0 Hz). Stage 1: With sodium hydride in tetrahydrofuran, dimethyl sulfoxide, Time= 0.5h, T= 1 - 50 °C Stage 2: in tetrahydrofuran, dimethyl sulfoxide, Time= 1h, Heating / reflux Stage 3: With water Patent; Takeda Chemical Industries, Ltd.; EP1357115; (2003); (A1) English View in Reaxys

O O O

O O O O

Rx-ID: 24790972 View in Reaxys 8/276 Yield

Conditions & References 74 :To a mixture of 5-formyl-2-hydroxybenzoic acid (15.34 g) and N,N-dimethylformamide (150 mL) was added sodium hydride (60percent, oil, 9.24 g) under ice-cooling. The reaction mixture was stirred at room temperature for 30 min., and then chloromethyl methyl ether (29.7 g) was added to the reaction mixture under ice-cooling. The reaction mixture was further stirred at room temperature for 15 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give methoxymethyl 5-formyl-2-methoxymethoxybenzoate as a colorless oil (14.23 g, 61percent) from a fraction eluted with ethyl acetate-hexane (2:3, v/v).<1>H-NMR (CDCl3) delta : 3.52 (3H, s), 3.57 (3H, s), 5.36 (2H, s), 5.48 (2H, s), 7.32-7.37 (1H, m), 7.96-8.04 (1H, m), 8.33-8.37 (1H, m), 9.93 (1H, s). [0518] To a mixture of dimethyl sulfoxide (100 mL) and tetrahydrofuran (300 mL) was added sodium hydride (60percent, oil, 3.58 g) at room temperature. The reaction mixture was stirred at 50 DEG C for 1.5 hrs. The reaction mixture was allowed to warm to room temperature, and then ethyl triphenylphosphonium bromide (27.03 g) was added. The mixture was stirred at room temperature for 30 min. To the reaction mixture was added a solution (50 mL) of methoxymethyl 5-formyl-2-methoxymethoxybenzoate (14.23 g) in dimethyl sulfoxide and the mixture was heated under reflux for 1 hr. Water was added to the reaction mixture, and the mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give a colorless oil from a fraction eluted with ethyl acetate-hexane (1:8, v/v). A mixture of the obtained oil, 5percent palladium carbon (7.0 g) and tetrahydrofuran (300 mL) was subjected to catalytic hydrogenation at room temperature and 1 atm. After filtering off the catalyst, the solvent was evaporated under reduced pressure to give methyl 2-methoxymethoxy-5-propylbenzoate as an oil (6.06 g, 45percent).<1>H-NMR (CDCl3) delta : 0.93 (3H, t, J=7.2 Hz), 1.52-1.72 (2H, m), 2.55 (2H, t, J=7.6 Hz), 3.52 (3H,

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s), 3.89 (3H, s), 5.22 (2H, s), 7.10 (1H, d, J=8.4 Hz), 7.25 (1H, dd, J=8.4, 2.2 Hz), 7.59 (1H, d, J=2.2 Hz). [0519] To a mixture of methyl 2-methoxymethoxy-5-propylbenzoate (6.06 g) and tetrahydrofuran (200 mL) was added lithium aluminum hydride (0.96 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. To the mixture was added sodium sulfate 10 hydrate (8.18 g) and the mixture was further stirred at room temperature for 30 min. The insoluble materials were removed by filtration, and the filtrate was concentrated to give (2-methoxymethoxy-5propylphenyl)methanol as an oil (4.98 g, 93percent). <1>H-NMR (CDCl3) delta : 0.93 (3H, t, J=7.2 Hz), 1.55-1.71 (2H, m), 2.28 (1H, t, J=6.4 Hz), 2.53 (2H, t, J=7.4 Hz), 3.49 (3H, s), 4.68 (2H, d, J=6.4 Hz), 5.21 (2H, s), 6.98-7.11 (3H, m). [0520] A mixture of (2-methoxymethoxy-5-propylphenyl)methanol (4.98 g), activated manganese dioxide (15.0 g) and ethyl acetate (300 ml) was stirred at room temperature for 15 hrs. Manganese dioxide was removed by filtration and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to give 2-methoxymethoxy-5-propylbenzaldehyde as an oil (4.19 g, 85percent) from a fraction eluted with ethyl acetate-hexane (1:4, v/v).<1>H-NMR (CDCl3) delta : 0.92 (3H, t, J=7.2 Hz), 1.52-1.68 (2H, m), 2.56 (2H, t, J=7.4 Hz), 3.52 (3H, s), 5.28 (2H, s), 7.13 (1H, d, J=8.8 Hz), 7.35 (1H, dd, J=8.8, 2.2 Hz), 7.65 (1H, d, J=2.2 Hz), 10.49 (1H, s). [0521] A mixture of 2-methoxymethoxy-5-propylbenzaldehyde (4.15 g), methyl methylthiomethyl sulfoxide (4.94 g), 40percent solution of benzyltrimethylammonium hydroxide in methanol (4 mL) and tetrahydrofuran (100 mL) was heated under reflux for 24 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. A mixture of the obtained residue and 10percent hydrogen chloride-methanol (100 mL) was heated under reflux for 15 hrs. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (1.65 g, 40percent) of methyl 2-(2-hydroxy-5-propyl)phenylacetate from a fraction eluted with ethyl acetate-hexane (1:6, v/v). Recrystallization from isopropyl ether-hexane gave colorless prism crystals. melting point: 74-75 DEG C. Stage 1: With sodium hydride in tetrahydrofuran, dimethyl sulfoxide, Time= 0.5h, T= 1 - 30 °C Stage 2: in tetrahydrofuran, dimethyl sulfoxide, Time= 1h, Heating / reflux Patent; Takeda Chemical Industries, Ltd.; EP1357115; (2003); (A1) English View in Reaxys

O O

O N

H O

S O

O N

H O

S O

Rx-ID: 25857190 View in Reaxys 9/276 Yield

Conditions & References 1.n :n) (3aR,7S,7aS)-7-[4-Methoxy-3-((Z)-propenyl)-benzyl]-2,2-dimethyl-5,5-dioxo- hexahydro-1-oxa-5lambda*6*thia-3-aza-indene-3-carboxylic acid tert-butyl ester; To a suspension of ethyl-triphenylphosphoniumbromide (0.52 g, 1.36 mmol) in anhydrous THF (25 ml_) is added under Argon a 1 M NaHMDS-solution in THF (1.5 ml_, 1 ,5 mmol) and the reaction mixture is stirred for 45 min at 30-35 0C. To the resulting orange solution is added a solution of (3aR,7S,7aS)-7-(3-formyl-4-methoxy-benzyl)-2,2-dimethyl-5,5-dioxo- hexahydro-1-oxa-5lambda*6*-thia-3-aza-indene-3-carboxylic acid tert-butyl ester (0.35 g, 0.75 mmol) in THF (5 ml.) at 0-5 0C. The reaction mixture is stirred at 25 0C for 3 h. After addition of NH4CI-solution (10 ml_) the product is extracted with EtOAc. The combined organic layers are washed with brine, dried over MgSO4 and evaporated. The pure product is obtained after purification by flash-chromatography on silica gel (hexane-EtOAc 5:2 to 2: 1 ) as a white foam: TLC (hexane-EtOAc 2:1 ) Rf=0.40; ESIMS [M+H+NH3] +=483; 1H-NMR (400 MHz, CDCI3): δ 7.05 (d, J=I Hz, 1 H), 7.03 (d, J=7Hz, 1 H), 6.84 (d, J=7 Hz, 1 H), 6.53 (d, J=10 Hz, 1 H), 5.86 (m, 1 H), 3.93 (s, 3H), 3.7-3.9 (m, 2H), 3.39 (t, J=12 Hz, 1 H), 3.0 (m, 3H), 2.71 (m, 2H), 2.58 (m, 1 H), 1.83 (d, J=7Hz, 3H), 1.64 (bs, 6H), 1.48 (s, 9H). Stage 1: With sodium hexamethyldisilazane in tetrahydrofuran, Time= 0.75h, T= 30 - 35 °C Stage 2: in tetrahydrofuran, Time= 3h, T= 0 - 25 °C Stage 3: With water, ammonium chloride in tetrahydrofuran Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2007/93621; (2007); (A1) English View in Reaxys

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O O

S O

Rx-ID: 36113919 View in Reaxys 10/276 Yield 80 %

Conditions & References Stage 1: With sodium hydride in tetrahydrofuran, Time= 0.166667h, T= 20 °C , Inert atmosphere Stage 2: in tetrahydrofuran, Time= 20h, T= 20 °C , Reflux, Inert atmosphere Chang, Meng-Yang; Wu, Ming-Hao; Chen, Yeh-Long; Organic Letters; vol. 15; nb. 11; (2013); p. 2822 - 2825 View in Reaxys O

ethyltriphenylphosphonium salt Br

Rx-ID: 9574979 View in Reaxys 11/276 Yield 45 %

Conditions & References Stage 1: With n-butyllithium in tetrahydrofuran, hexane, Time= 1h, T= -78 °C Stage 2: in tetrahydrofuran, hexane, Time= 2h, Wittig reaction Martinez, Valentin; Burgos, Carolina; Alvarez-Builla, Julio; Fernandez, Geronimo; Domingo, Alberto; GarciaNieto, Raquel; Gago, Federico; Manzanares, Ignacio; Cuevas, Carmen; Vaquero, Juan J.; Journal of Medicinal Chemistry; vol. 47; nb. 5; (2004); p. 1136 - 1148 View in Reaxys

O O

Rx-ID: 33844846 View in Reaxys 12/276 Yield 86 %

Conditions & References With sodium hydroxide in methanol, Time= 20h, Inert atmosphere, Reflux Chang, Meng-Yang; Wu, Ming-Hao; Tai, Hang-Yi; Organic Letters; vol. 14; nb. 15; (2012); p. 3936 - 3939 View in Reaxys

O O O O

O O

Rx-ID: 33844881 View in Reaxys 13/276 Yield 88 %

Conditions & References With sodium hydroxide in methanol, Inert atmosphere, Reflux Chang, Meng-Yang; Wu, Ming-Hao; Tai, Hang-Yi; Organic Letters; vol. 14; nb. 15; (2012); p. 3936 - 3939 View in Reaxys

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HO O

N E

Rx-ID: 25265681 View in Reaxys 14/276 Yield

Conditions & References 7 : β-Methyl-5-chloro-2-hydroxynitrostyrene EXAMPLE 7 β-Methyl-5-chloro-2-hydroxynitrostyrene 5-Chloro-2-hydroxybenzaldehyde (15.6 g.) and n-butylamine (9.12 g.) were refluxed in dry benzene (100 ml.) using Dean-Stark water separator for 3 hours. The benzene phase was concentrated. The crude aldimine (23 g.), nitroethane (23 ml.) and glacial acetic acid were refluxed for 1 hour. The reaction mixture was diluted with ice-water to get the oily final product. The oily product was twice crystallized from ethanol to get the title product; m.p. 104-6° C. With N-butylamine in acetic acid, benzene Patent; Sarabhai Research Centre; US3985761; (1976); (A1) English View in Reaxys Br

HO O

Rx-ID: 25265685 View in Reaxys 15/276 Yield

Conditions & References 9 : β-Methyl-5-bromo-2-hydroxynitrostyrene EXAMPLE 9 β-Methyl-5-bromo-2-hydroxynitrostyrene 5-Bromo-2-hydroxybenzaldehyde (20.1 g.) and n-butylamine (9.12 g.) were refluxed in dry benzene (100 ml.) using Dean-Stark water separator for 3 hours. The benzene phase was concentrated. The crude aldimine (25 g.), nitroethane (25 ml.) and glacial acetic acid (75 ml.) were refluxed for 1 hour. The reaction mixture was diluted with ice-water to get the crude product which was crystallized from hexane to get the title product; m.p. 95-7° C. With N-butylamine in acetic acid, benzene Patent; Sarabhai Research Centre; US3985761; (1976); (A1) English View in Reaxys

OH E

O O

Rx-ID: 25268041 View in Reaxys 16/276 Yield

Conditions & References 1 : β-Methyl-3-hydroxynitrostyrene EXAMPLE 1 β-Methyl-3-hydroxynitrostyrene 3-hydroxybenzaldehyde (12.2 g) and n-butylamine (9.12 g.) were refluxed in dry benzene (100 ml.) using Dean-Stark water separator for 3 hours. Benzene phase was concentrated. The residual solid, the crude aldimine, was filtered after cooling. The aldimine (17.5 g.) nitroethane (17.5 ml.) and glacial acetic acid (52 ml.) were heated for 30 minutes at 100° C. The reaction mixture was diluted with cold water. The crude title product thus obtained was crystallized from aqueous ethanol; m.p. 96°-98° C.

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With N-butylamine in acetic acid, benzene Patent; Sarabhai Research Centre; US3985761; (1976); (A1) English View in Reaxys

N Cl

Cl O

Rx-ID: 25268473 View in Reaxys 17/276 Yield

Conditions & References 5 : β-Methyl-3-chloro-4-hydroxynitrostyrene EXAMPLE 5 β-Methyl-3-chloro-4-hydroxynitrostyrene 3-Chloro-4-hydroxybenzaldehyde (15.6 g.) and n-butylamine (9.12 g.) were refluxed in dry benzene (150 ml.) at 100° C, by azeotropically distilling off the water of reaction. Benzene phase was concentrated to get the oily aldimine. The aldimine (21 g), nitroethane (21 ml.) and formic acid (65 ml.) were refluxed for 1 hour. The reaction mixture was diluted with ice-water. The crude product thus obtained was crystallized from aqueous ethanol to get the title product melting at 91°-93° C. With formic acid, N-butylamine in benzene Patent; Sarabhai Research Centre; US3985761; (1976); (A1) English View in Reaxys

N Br

Br O

Rx-ID: 25268476 View in Reaxys 18/276 Yield

Conditions & References 3 : β-Methyl-3-bromo-4-hydroxynitrostyrene EXAMPLE 3 β-Methyl-3-bromo-4-hydroxynitrostyrene 3-Bromo-4-hydroxybenzaldehyde (20.1 g.) and n-butylamine (9.12 g.) were refluxed in dry toluene (100 ml.) using Dean-Stark water separator for 4 hours. Organic phase was concentrated. The oily intermediate (25.6 g.), nitroethane (25.5 ml.) and propionic acid (77 ml.) were heated at 110° C for 1 hour. The reaction mixture was poured into crushed ice. The solid product was filtered off and crystallized from aqueous ethanol to obtain the title product, m.p. 122°-24° C. With propionic acid, N-butylamine in toluene Patent; Sarabhai Research Centre; US3985761; (1976); (A1) English View in Reaxys I

I Z

ethylphosphonium salt

Rx-ID: 38668418 View in Reaxys 19/276 Yield

Conditions & References With n-butyllithium in tetrahydrofuran, hexane, Time= 0.0375h, T= 0 °C , Inert atmosphere, Wittig Olefination Zhang, Wenhan; Ready, Joseph M.; Angewandte Chemie - International Edition; vol. 53; nb. 34; (2014); p. 8980 8984; Angew. Chem.; vol. 53-126; nb. 34; (2014); p. 9126 - 9130,5 View in Reaxys

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O E

O O

Rx-ID: 42849376 View in Reaxys 20/276 Yield

Conditions & References

55 %

Stage 1:Time= 2h, T= 0 - 20 °C , Grignard Reaction Stage 2: With toluene-4-sulfonic acid in toluene, Heating Patil, Sagar N.; Tilve, Santosh G.; Tetrahedron Letters; vol. 57; nb. 30; (2016); p. 3371 - 3375 View in Reaxys

O O O

E O

Rx-ID: 13131755 View in Reaxys 21/276 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium / diethyl ether / 2 h 1.2: 81 percent / diethyl ether; toluene / 20 °C 2.1: 64 percent / silica gel / dioxane / 0.05 h / microwave irradiation With silica gel, magnesium in 1,4-dioxane, diethyl ether, 1.2: Grignard reaction Sharma, Anuj; Joshi, Bhupendra P.; Sinha, Arun K.; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2231 - 2235 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 3 h 2: CuSO4 / toluene / 2 h / Heating With copper(II) sulfate in tetrahydrofuran, toluene, 1: Addition / 2: Dehydration Poplawski; Lozowicka; Dubis; Lachowska; Witkowski; Siluk; Petrusewicz; Kaliszan; Cybulski; Strzalkowska; Chilmonczyk; Journal of Medicinal Chemistry; vol. 43; nb. 20; (2000); p. 3671 - 3676 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran 2: anhyd. CuSO4 / toluene With copper(II) sulfate in tetrahydrofuran, toluene, 1: Grignard reaction / 2: Dehydration Poplewski, Janusz; Lozowicka, Bozena; Dubis, Alina T.; Lachowska, Barbara; Winiecki, Zbigiew; Nawrot, Jan; Pest Management Science; vol. 56; nb. 6; (2000); p. 560 - 564 View in Reaxys Reaction Steps: 2 1: 80 percent / I2 / tetrahydrofuran / 2 h / 20 °C 2: 58 percent / CuSO4 / toluene / 4 h / Heating With iodine, copper(II) sulfate in tetrahydrofuran, toluene, 1: Grignard reaction / 2: Dehydration Wolska; Poplawski; Lozowicka; Polish Journal of Chemistry; vol. 72; nb. 10; (1998); p. 2331 - 2341 View in Reaxys

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O E

O O

Rx-ID: 13136617 View in Reaxys 22/276 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium / diethyl ether / 2 h 1.2: 79 percent / diethyl ether; toluene / 20 °C 2.1: 74 percent / silica gel / dioxane / 0.05 h / microwave irradiation With silica gel, magnesium in 1,4-dioxane, diethyl ether, 1.2: Grignard reaction Sharma, Anuj; Joshi, Bhupendra P.; Sinha, Arun K.; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2231 - 2235 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 3 h 2: CuSO4 / toluene / 2 h / Heating With copper(II) sulfate in tetrahydrofuran, toluene, 1: Addition / 2: Dehydration Poplawski; Lozowicka; Dubis; Lachowska; Witkowski; Siluk; Petrusewicz; Kaliszan; Cybulski; Strzalkowska; Chilmonczyk; Journal of Medicinal Chemistry; vol. 43; nb. 20; (2000); p. 3671 - 3676 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran 2: anhyd. CuSO4 / toluene With copper(II) sulfate in tetrahydrofuran, toluene, 1: Grignard reaction / 2: Dehydration Poplewski, Janusz; Lozowicka, Bozena; Dubis, Alina T.; Lachowska, Barbara; Winiecki, Zbigiew; Nawrot, Jan; Pest Management Science; vol. 56; nb. 6; (2000); p. 560 - 564 View in Reaxys Reaction Steps: 2 1: toluene; diethyl ether / 16 h / 0 °C / |Milling 2: silica gel / 1,4-dioxane / |Microwave irradiation With silica gel in 1,4-dioxane, diethyl ether, toluene Neve, Juliette E.; Wijesekera, Hasanthi P.; Duffy, Sandra; Jenkins, Ian D.; Ripper, Justin A.; Teague, Simon J.; Campitelli, Marc; Garavelas, Agatha; Nikolakopoulos, George; Le, Phuc V.; De A. Leone, Priscila; Pham, Ngoc B.; Shelton, Philip; Fraser, Neil; Carroll, Anthony R.; Avery, Vicky M.; McCrae, Christopher; Williams, Nicola; Quinn, Ronald J.; Journal of Medicinal Chemistry; vol. 57; nb. 4; (2014); p. 1252 - 1275 View in Reaxys

Rx-ID: 22148500 View in Reaxys 23/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: P2O5; petroleum ether; benzene With diethyl ether, phosphorus pentoxide, Petroleum ether, benzene Kon; Spickett; Journal of the Chemical Society; (1949); p. 2725 View in Reaxys Reaction Steps: 3 1: (R)-1,1'-Bi-2-naphthol; titanium(IV) isopropylate / diethyl ether / -20 °C / |Inert atmosphere

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2: sodium hydride / tetrahydrofuran / 40 °C / |Inert atmosphere 3: 1,2-bis(diphenylphosphino)ethane nickel(II) chloride / diethyl ether; toluene / 24 h / 20 °C / |Inert atmosphere With titanium(IV) isopropylate, 1,2-bis(diphenylphosphino)ethane nickel(II) chloride, (R)-1,1'-Bi-2-naphthol, sodium hydride in tetrahydrofuran, diethyl ether, toluene Yonova, Ivelina M.; Johnson, A. George; Osborne, Charlotte A.; Moore, Curtis E.; Morrissette, Naomi S.; Jarvo, Elizabeth R.; Angewandte Chemie - International Edition; vol. 53; nb. 9; (2014); p. 2422 - 2427; Angew. Chem.; vol. 126; nb. 9; (2014); p. 2454 - 2459,6 View in Reaxys

Rx-ID: 11336724 View in Reaxys 24/276 Yield

Conditions & References Reaction Steps: 3 1.1: Et3N; CuI / PdCl2(PPh3)3 / tetrahydrofuran / 4 h / Heating 2.1: t-BuOK / tetrahydrofuran / 1 h / 0 °C 2.2: tetrahydrofuran / 16 h / 20 °C 3.1: K2CO3 / methanol / 2 h With copper(l) iodide, potassium tert-butylate, potassium carbonate, triethylamine, [Pd(PPh 3)2Cl2] in tetrahydrofuran, methanol Barluenga, Jose; Andina, Facundo; Aznar, Fernando; Valde, Carlos; Organic Letters; vol. 9; nb. 21; (2007); p. 4143 - 4146 View in Reaxys Br

Br Z

Rx-ID: 19263733 View in Reaxys 25/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) Mg / 1.) ether, reflux, 2 h; 2.) ether, 12 h, room temp. 2: potassium hydrogen sulfate, phosphorus pentoxide, 4-tert-butylcatechol / 230 °C With P2O5, potassium hydrogensulfate, 3,4-dihydroxy-1-tert-butylbenzene, magnesium Padwa, Albert; Rieker, William F.; Rosenthal, Robert J.; Journal of the American Chemical Society; vol. 107; nb. 6; (1985); p. 1710 - 1717 View in Reaxys Reaction Steps: 3 1: 1.) Mg / 1.) ether, reflux, 2 h; 2.) ether, 12 h, room temp. 2: 87 percent / potassium hydrogen sulfate, phosphorus pentoxide, 4-tert-butylcatechol / 230 °C 3: thioxanthen-9-one / benzene / 14.5 h / Irradiation With P2O5, potassium hydrogensulfate, 9H-thioxanthen-9-one, 3,4-dihydroxy-1-tert-butylbenzene, magnesium in benzene Padwa, Albert; Rieker, William F.; Rosenthal, Robert J.; Journal of the American Chemical Society; vol. 107; nb. 6; (1985); p. 1710 - 1717 View in Reaxys

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Rx-ID: 34415761 View in Reaxys 26/276 Yield

Conditions & References Reaction Steps: 2 1: C{N(2,6-iPr2C6H3)CH}2 / 1,3,5-trimethyl-benzene / 24 h / 130 °C / |Inert atmosphere 2: C{N(2,6-iPr2C6H3)CH}2; bis(1,5-cyclooctadiene)nickel (0) / benzene-d6 / 15 h / 130 °C / |Inert atmosphere With bis(1,5-cyclooctadiene)nickel (0), C{N(2,6-iPr2C6H3)CH}2 in benzene-d6, 1,3,5-trimethyl-benzene, 2: |Tishchenko-Claisen Dismutation Hoshimoto, Yoichi; Hayashi, Yukari; Suzuki, Haruka; Ohashi, Masato; Ogoshi, Sensuke; Angewandte Chemie - International Edition; vol. 51; nb. 43; (2012); p. 10812 - 10815; Angew. Chem.; vol. 124; nb. 43; (2012); p. 10970 10973,4 View in Reaxys Reaction Steps: 2 1: C{N(2,6-iPr2C6H3)CH}2; bis(1,5-cyclooctadiene)nickel (0) / toluene / 24 h / 130 °C / |Inert atmosphere 2: C{N(2,6-iPr2C6H3)CH}2; bis(1,5-cyclooctadiene)nickel (0) / benzene-d6 / 15 h / 130 °C / |Inert atmosphere With bis(1,5-cyclooctadiene)nickel (0), C{N(2,6-iPr2C6H3)CH}2 in benzene-d6, toluene, 2: |Tishchenko-Claisen Dismutation Hoshimoto, Yoichi; Hayashi, Yukari; Suzuki, Haruka; Ohashi, Masato; Ogoshi, Sensuke; Angewandte Chemie - International Edition; vol. 51; nb. 43; (2012); p. 10812 - 10815; Angew. Chem.; vol. 124; nb. 43; (2012); p. 10970 10973,4 View in Reaxys

E O

Rx-ID: 12502402 View in Reaxys 27/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys Reaction Steps: 2 1: diethyl ether 2: H2SO4 / 60 °C With sulfuric acid in diethyl ether Greca, Marina Della; Monaco, Pietro; Pollio, Antonino; Previtera, Lucio; Phytochemistry (Elsevier); vol. 31; nb. 12; (1992); p. 4119 - 4124 View in Reaxys Reaction Steps: 2 1: toluene; diethyl ether / 16 h / 0 °C 2: silica gel / 1,4-dioxane / |Microwave irradiation With silica gel in 1,4-dioxane, diethyl ether, toluene

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Neve, Juliette E.; Wijesekera, Hasanthi P.; Duffy, Sandra; Jenkins, Ian D.; Ripper, Justin A.; Teague, Simon J.; Campitelli, Marc; Garavelas, Agatha; Nikolakopoulos, George; Le, Phuc V.; De A. Leone, Priscila; Pham, Ngoc B.; Shelton, Philip; Fraser, Neil; Carroll, Anthony R.; Avery, Vicky M.; McCrae, Christopher; Williams, Nicola; Quinn, Ronald J.; Journal of Medicinal Chemistry; vol. 57; nb. 4; (2014); p. 1252 - 1275 View in Reaxys

O O

Rx-ID: 12508471 View in Reaxys 28/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys Reaction Steps: 2 1: 65 percent 2: 67 percent / <(C6H5)3P>2NiCl2 / benzene; diethyl ether / Heating With NiCl2((PPh3)P)2 in diethyl ether, benzene Wenkert, Ernest; Fernandes, Joao Battista; Michelotti, Enrique L.; Swindell, Charles S.; Synthesis; nb. 9; (1983); p. 701 - 703 View in Reaxys Reaction Steps: 2 1: (i) Li, Et2O, (ii) /BRN= 473899/ 2: TsOH / benzene With toluene-4-sulfonic acid in benzene Witiak; Kakodkar; Brunst; Baldwin; Rahwan; Journal of Medicinal Chemistry; vol. 21; nb. 12; (1978); p. 1313 1315 View in Reaxys

O O O

O O

Rx-ID: 13152629 View in Reaxys 29/276 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium / diethyl ether / 2 h 1.2: 88 percent / diethyl ether; toluene / 20 °C 2.1: 71 percent / silica gel / dioxane / 0.05 h / microwave irradiation With silica gel, magnesium in 1,4-dioxane, diethyl ether, 1.2: Grignard reaction Sharma, Anuj; Joshi, Bhupendra P.; Sinha, Arun K.; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2231 - 2235 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran / 3 h 2: CuSO4 / toluene / 2 h / Heating With copper(II) sulfate in tetrahydrofuran, toluene, 1: Addition / 2: Dehydration Poplawski; Lozowicka; Dubis; Lachowska; Witkowski; Siluk; Petrusewicz; Kaliszan; Cybulski; Strzalkowska; Chilmonczyk; Journal of Medicinal Chemistry; vol. 43; nb. 20; (2000); p. 3671 - 3676

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View in Reaxys Reaction Steps: 2 1: tetrahydrofuran 2: anhyd. CuSO4 / toluene With copper(II) sulfate in tetrahydrofuran, toluene, 1: Grignard reaction / 2: Dehydration Poplewski, Janusz; Lozowicka, Bozena; Dubis, Alina T.; Lachowska, Barbara; Winiecki, Zbigiew; Nawrot, Jan; Pest Management Science; vol. 56; nb. 6; (2000); p. 560 - 564 View in Reaxys

OH E

Rx-ID: 15843607 View in Reaxys 30/276 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 20 °C 1.2: 91 percent / tetrahydrofuran; hexane / 3 h / 20 °C 2.1: 99 percent / KOH / methanol; H2O / 65 °C With potassium hydroxide, n-butyllithium in tetrahydrofuran, methanol, hexane, water, 1.1: E-selective Wittig reaction / 1.2: E-selective Wittig reaction / 2.1: Hydrolysis Lindsley, Craig W.; Chan, Lawrence K.; Goess, Brian C.; Joseph, Reni; Shair, Matthew D.; Journal of the American Chemical Society; vol. 122; nb. 2; (2000); p. 422 - 423 View in Reaxys

KO H

Rx-ID: 20517557 View in Reaxys 31/276 Yield

Conditions & References Reaction Steps: 2 2: p-toluenesulphonic acid / benzene / 0.33 h / Heating With toluene-4-sulfonic acid in benzene Caldwell, Richard A.; Creed, David; DeMarco, D. C.; Melton, Lynn A.; Ohta, Hiroyuki; Wine, Paul H.; Journal of the American Chemical Society; vol. 102; nb. 7; (1980); p. 2369 - 2377 View in Reaxys

Rx-ID: 22108551 View in Reaxys 32/276 Yield

Conditions & References Reaction Steps: 2 2: phosphorus pentoxide; benzene With phosphorus pentaoxide, benzene Quelet; Bulletin de la Societe Chimique de France; vol. <4> 45; (1929); p. 78; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 182; (1926); p. 1284 View in Reaxys Reaction Steps: 2 2: sodium disulfate / 150 °C With sodium pyrosulfate Ziegler; Tiemann; Chemische Berichte; vol. 55; (1922); p. 3414 View in Reaxys Reaction Steps: 2

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1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: toluene-4-sulfonic acid / benzene / 3 h / Inert atmosphere; Reflux; Dean-Stark With toluene-4-sulfonic acid in tetrahydrofuran, benzene Daniel, Paige E.; Weber, Alexandria E.; Malcolmson, Steven J.; Organic Letters; vol. 19; nb. 13; (2017); p. 3490 3493 View in Reaxys

Rx-ID: 35784495 View in Reaxys 33/276 Yield

Conditions & References With 4-methyl-morpholine in acetonitrile, T= 20 °C , Inert atmosphere Zhu, Jian-Bo; Wang, Peng; Liao, Saihu; Tang, Yong; Organic Letters; vol. 15; nb. 12; (2013); p. 3054 - 3057 View in Reaxys

Rx-ID: 35784499 View in Reaxys 34/276 Yield

HO O O

Rx-ID: 35784507 View in Reaxys 35/276 Yield

O O

Rx-ID: 35784519 View in Reaxys 36/276 Yield

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OH O

E O

Rx-ID: 37271659 View in Reaxys 37/276 Yield

Conditions & References Reaction Steps: 2 1.1: C21H36N3PRu / acetone / 1.5 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.25 h / 0 °C / |Inert atmosphere 2.2: 0 - 20 °C / |Inert atmosphere With n-butyllithium, C21H36N3PRu in tetrahydrofuran, acetone Murphy, Stephen K.; Bruch, Achim; Dong, Vy M.; Angewandte Chemie - International Edition; vol. 53; nb. 9; (2014); p. 2455 - 2459; Angew. Chem.; vol. 126; nb. 09; (2014); p. 2487 - 2491,5 View in Reaxys

ethyltriphenylphosphonium halide

Rx-ID: 40011333 View in Reaxys 38/276 Yield

Conditions & References With n-butyllithium in tetrahydrofuran, hexane, T= 0 - 20 °C Sanjun, Ana M.; Rashid, Muhammad A.; Garca-Garca, Patricia; Martnez-Cuezva, Alberto; Fernndez-Rodrguez, Manuel A.; Rodrguez, Flix; Sanz, Roberto; Chemistry - A European Journal; vol. 21; nb. 7; (2015); p. 3042 3052 View in Reaxys

Rx-ID: 12018514 View in Reaxys 39/276 Yield

Conditions & References Reaction Steps: 3 1: 86 percent / LiAlH4 / tetrahydrofuran / 12 h / 40 °C 2: 77 percent / NaH / tetrahydrofuran / 20 h / Heating 3: 52 percent / RuClH(CO)(PPh3)3 / toluene / 2 h / 60 °C With lithium aluminium tetrahydride, sodium hydride, [(C6H5)3P]3Ru(CO)(Cl)H in tetrahydrofuran, toluene Pathak, Rakhi; Panayides, Jenny-Lee; Jeftic, Tanya D.; De Koning, Charles B.; Van Otterlo, Willem A.L.; South African Journal of Chemistry; vol. 60; (2007); p. 1 - 7 View in Reaxys Reaction Steps: 3 1: 86 percent / LiAlH4 / tetrahydrofuran / 12 h / 40 °C 2: 77 percent / NaH / tetrahydrofuran / 20 h / Heating 3: [RuClH(CO)(PPh3)3] / toluene / 80 °C With lithium aluminium tetrahydride, sodium hydride, [(C6H5)3P]3Ru(CO)(Cl)H in tetrahydrofuran, toluene Van Otterlo, Willem A. L.; Pathak, Rakhi; De Koning, Charles B.; Synlett; nb. 12; (2003); p. 1859 - 1861 View in Reaxys

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O E

Rx-ID: 14081472 View in Reaxys 40/276 Yield

Conditions & References Reaction Steps: 4 1: 89 percent / diethyl ether / 20 °C 2: 58 percent / activated manganese dioxide / benzene / 0.67 h / Heating 3: 87 percent / palladium dichloride bis-acetonitrile / CH2Cl2 / 72 h / Heating 4: borane/dimethyl sulphide complex / oxazaborolidine based catalyst / tetrahydrofuran / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide, borane, oxazaborolidine based catalyst in tetrahydrofuran, diethyl ether, dichloromethane, benzene, 4: Corey-Bakshi-Shibata asymmetric reduction De Koning, Charles B.; Giles, Robin G.F.; Green, Ivan R.; Jahed, Nazeem M.; Tetrahedron; vol. 59; nb. 17; (2003); p. 3175 - 3182 View in Reaxys Reaction Steps: 4 1: diethyl ether / 0.67 h / 25 °C 2: MnO2 / benzene / 0.75 h / Heating 3: PdCl2(CH3CN)2 / CH2Cl2 / 72 h / 35 °C 4: BH3*(CH3)2S / Corey-Bakshi-Shibata catalyst / tetrahydrofuran; toluene / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide borane complex, (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol in tetrahydrofuran, diethyl ether, dichloromethane, toluene, benzene, 4: Corey-Bakshi-Shibata reduction De Koning, Charles B; Giles, Robin G.F; Green, Ivan R; Jahed, Nazeem M; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4199 - 4201 View in Reaxys

O E

Rx-ID: 14081473 View in Reaxys 41/276 Yield

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With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide borane complex, (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol in tetrahydrofuran, diethyl ether, dichloromethane, toluene, benzene, 4: Corey-Bakshi-Shibata reduction De Koning, Charles B; Giles, Robin G.F; Green, Ivan R; Jahed, Nazeem M; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4199 - 4201 View in Reaxys

O O

O HO

Rx-ID: 14088561 View in Reaxys 42/276 Yield

Conditions & References Reaction Steps: 4 1: 93 percent / diethyl ether / 0.67 h / 20 °C 2: 57 percent / activated manganese dioxide / benzene / 0.67 h / Heating 3: 94 percent / palladium dichloride bis-acetonitrile / CH2Cl2 / 72 h / Heating 4: borane/dimethyl sulphide complex / oxazaborolidine based catalyst / tetrahydrofuran / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide, borane, oxazaborolidine based catalyst in tetrahydrofuran, diethyl ether, dichloromethane, benzene, 4: Corey-Bakshi-Shibata asymmetric reduction De Koning, Charles B.; Giles, Robin G.F.; Green, Ivan R.; Jahed, Nazeem M.; Tetrahedron; vol. 59; nb. 17; (2003); p. 3175 - 3182 View in Reaxys Reaction Steps: 4 1: diethyl ether / 0.67 h / 25 °C 2: MnO2 / benzene / 0.75 h / Heating 3: PdCl2(CH3CN)2 / CH2Cl2 / 72 h / 35 °C 4: BH3*(CH3)2S / Corey-Bakshi-Shibata catalyst / tetrahydrofuran; toluene / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide borane complex, (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol in tetrahydrofuran, diethyl ether, dichloromethane, toluene, benzene, 4: Coreyy-Bakshi-Shibata reduction De Koning, Charles B; Giles, Robin G.F; Green, Ivan R; Jahed, Nazeem M; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4199 - 4201 View in Reaxys

O O

Rx-ID: 14088562 View in Reaxys 43/276 Yield

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3: PdCl2(CH3CN)2 / CH2Cl2 / 72 h / 35 °C 4: BH3*(CH3)2S / Corey-Bakshi-Shibata catalyst / tetrahydrofuran; toluene / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide borane complex, (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol in tetrahydrofuran, diethyl ether, dichloromethane, toluene, benzene, 4: Coreyy-Bakshi-Shibata reduction De Koning, Charles B; Giles, Robin G.F; Green, Ivan R; Jahed, Nazeem M; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4199 - 4201 View in Reaxys

O O

OH O

Rx-ID: 14092270 View in Reaxys 44/276 Yield

Conditions & References Reaction Steps: 4 1: 80 percent / diethyl ether / 20 °C 2: 60 percent / activated manganese dioxide / benzene / 0.67 h / Heating 3: 81 percent / palladium dichloride bis-acetonitrile / CH2Cl2 / 72 h / Heating 4: borane/dimethyl sulphide complex / oxazaborolidine based catalyst / tetrahydrofuran / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide, borane, oxazaborolidine based catalyst in tetrahydrofuran, diethyl ether, dichloromethane, benzene, 4: Corey-Bakshi-Shibata asymmetric reduction De Koning, Charles B.; Giles, Robin G.F.; Green, Ivan R.; Jahed, Nazeem M.; Tetrahedron; vol. 59; nb. 17; (2003); p. 3175 - 3182 View in Reaxys Reaction Steps: 4 1: diethyl ether / 0.67 h / 25 °C 2: MnO2 / benzene / 0.75 h / Heating 3: PdCl2(CH3CN)2 / CH2Cl2 / 72 h / 35 °C 4: BH3*(CH3)2S / Corey-Bakshi-Shibata catalyst / tetrahydrofuran; toluene / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide borane complex, (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol in tetrahydrofuran, diethyl ether, dichloromethane, toluene, benzene, 4: Corey-Bakshi-Shibata reduction De Koning, Charles B; Giles, Robin G.F; Green, Ivan R; Jahed, Nazeem M; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4199 - 4201 View in Reaxys

O O

OH O

Rx-ID: 14092271 View in Reaxys 45/276 Yield

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Reaction Steps: 4 1: diethyl ether / 0.67 h / 25 °C 2: MnO2 / benzene / 0.75 h / Heating 3: PdCl2(CH3CN)2 / CH2Cl2 / 72 h / 35 °C 4: BH3*(CH3)2S / Corey-Bakshi-Shibata catalyst / tetrahydrofuran; toluene / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide borane complex, (S)-3,3-diphenyl-1-methyltetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborol in tetrahydrofuran, diethyl ether, dichloromethane, toluene, benzene, 4: Corey-Bakshi-Shibata reduction De Koning, Charles B; Giles, Robin G.F; Green, Ivan R; Jahed, Nazeem M; Tetrahedron Letters; vol. 43; nb. 23; (2002); p. 4199 - 4201 View in Reaxys

solid phase-bound -CH2OC(O)NH2

O O

Rx-ID: 16007446 View in Reaxys 46/276 Yield

Conditions & References Reaction Steps: 4 1: 95 percent / pyridine; piperidine / 1 h / Heating 2: 99 percent / Br2 / CHCl3 / 0 - 20 °C 3: 85 percent / NaN3 / dimethylformamide 4: 67 percent / Pd(PPh3)4 / benzene; diethyl ether / 20 °C With piperidine, pyridine, sodium azide, bromine, tetrakis(triphenylphosphine) palladium(0) in diethyl ether, chloroform, N,N-dimethyl-formamide, benzene, 1: Condensation / 2: Bromination / 3: Decarboxylation / 4: Addition Mohan, Ram S.; Gavardinas, Kostas; Kyere, Sampson; Whalen, Dale L.; Journal of Organic Chemistry; vol. 65; nb. 5; (2000); p. 1407 - 1413 View in Reaxys

O O

Z Si

Rx-ID: 36200607 View in Reaxys 47/276 Yield

Conditions & References Reaction Steps: 2 1.1: silver(l) oxide / diethyl ether / 10 h / 20 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C / |Inert atmosphere 2.2: 2 h / 0 - 20 °C / |Inert atmosphere With n-butyllithium, silver(l) oxide in tetrahydrofuran, diethyl ether, hexane, 2.1: |Wittig Olefination Strych, Sebastian; Trauner, Dirk; Angewandte Chemie - International Edition; vol. 52; nb. 36; (2013); p. 9509 9512; Angew. Chem.; vol. 125; nb. 36; (2013); p. 9687 - 9690,4 View in Reaxys

O O

O HO

Rx-ID: 37612133 View in Reaxys 48/276 Yield

Conditions & References With titanium tetrachloride, zinc in tetrahydrofuran, Time= 15h, T= 0 °C , Inert atmosphere, Reflux Han, Xin; Dong, Chune; Zhou, Hai-Bing; Advanced Synthesis and Catalysis; vol. 356; nb. 6; (2014); p. 1275 1280 View in Reaxys

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Rx-ID: 9475994 View in Reaxys 49/276 Yield

Conditions & References With boron trifluoride diethyl etherate in hexane, T= 20 °C , aldol Grob reaction Bidet; McGuigan; Andrei; Snoeck; De Clercq; Balzarini; Nucleosides, Nucleotides and Nucleic Acids; vol. 22; nb. 5-8; (2003); p. 817 - 819 View in Reaxys With boron trifluoride diethyl etherate in hexane, Time= 18h, T= 20 °C McGuigan, Christopher; Bidet, Olivier; Derudas, Marco; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Bioorganic and Medicinal Chemistry; vol. 17; nb. 8; (2009); p. 3025 - 3027 View in Reaxys

O O

Rx-ID: 36291797 View in Reaxys 50/276 Yield

Conditions & References Reaction Steps: 3 1: 18-crown-6 ether; potassium tert-butylate / dichloromethane / 18 h / 0 - 20 °C / |Inert atmosphere; |Schlenk technique 2: palladium diacetate; ruphos; potassium carbonate / toluene; water / 1.5 h / 85 °C / |Inert atmosphere; |Schlenk technique 3: tetrahydrofuran; diethyl ether / 0.25 h / -78 - 0 °C / |Inert atmosphere; |Schlenk technique With 18-crown-6 ether, potassium tert-butylate, palladium diacetate, potassium carbonate, ruphos in tetrahydrofuran, diethyl ether, dichloromethane, water, toluene, 1: |Wittig Olefination / 2: |Suzuki Coupling Hume, Paul A.; Furkert, Daniel P.; Brimble, Margaret A.; Organic Letters; vol. 15; nb. 17; (2013); p. 4588 - 4591 View in Reaxys Reaction Steps: 3 1: potassium tert-butylate; 18-crown-6 ether / dichloromethane / 20 °C / |Inert atmosphere 2: potassium carbonate; palladium diacetate; ruphos / water; toluene / 1.5 h / 85 °C / |Inert atmosphere 3: methyllithium / tetrahydrofuran / 0.5 h / -78 - 0 °C / |Inert atmosphere With 18-crown-6 ether, potassium tert-butylate, methyllithium, palladium diacetate, potassium carbonate, ruphos in tetrahydrofuran, dichloromethane, water, toluene, 2: |Suzuki Coupling Hume, Paul A.; Furkert, Daniel. P.; Brimble, Margaret A.; Journal of Organic Chemistry; vol. 79; nb. 11; (2014); p. 5269 - 5281 View in Reaxys Br

EtPPh3(+) halide

E O

Rx-ID: 9574985 View in Reaxys 51/276 Yield

Conditions & References Stage 1: With potassium tert-butylate in toluene, T= -30 - 20 °C Stage 2: With 2,2'-azo-bisisobutyronitrile, thiophenol in toluene, Time= 1h, T= 80 °C , Further stages.

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Bianchi, Dario A.; Rua, Federico; Kaufman, Teodoro S.; Tetrahedron Letters; vol. 45; nb. 2; (2004); p. 411 - 415 View in Reaxys

O E

O O HO

Rx-ID: 14081443 View in Reaxys 52/276 Yield

Conditions & References Reaction Steps: 6 1: 12 h / 180 °C 2: 6.64 g / potassium carbonate / dimethylformamide / 24 h / 80 °C 3: 93 percent / diethyl ether / 0.67 h / 20 °C 4: 57 percent / activated manganese dioxide / benzene / 0.67 h / Heating 5: 94 percent / palladium dichloride bis-acetonitrile / CH2Cl2 / 72 h / Heating 6: borane/dimethyl sulphide complex / oxazaborolidine based catalyst / tetrahydrofuran / 0.5 h / 25 °C With manganese(IV) oxide, dichloro bis(acetonitrile) palladium(II), dimethylsulfide, borane, potassium carbonate, oxazaborolidine based catalyst in tetrahydrofuran, diethyl ether, dichloromethane, N,N-dimethyl-formamide, benzene, 6: Corey-Bakshi-Shibata asymmetric reduction De Koning, Charles B.; Giles, Robin G.F.; Green, Ivan R.; Jahed, Nazeem M.; Tetrahedron; vol. 59; nb. 17; (2003); p. 3175 - 3182 View in Reaxys

O E

O O HO

Rx-ID: 14081444 View in Reaxys 53/276 Yield

H O

HI, I2

Rx-ID: 16481575 View in Reaxys 54/276 Yield

Conditions & References Reaction Steps: 3 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 64 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 3: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With lithium aluminium tetrahydride, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, dichloromethane Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360

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View in Reaxys Reaction Steps: 3 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 88 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 3: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With lithium aluminium tetrahydride, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, dichloromethane Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360 View in Reaxys Reaction Steps: 5 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 94 percent / PDC / dimethylformamide / Ambient temperature 3: 47 percent / NaBH4 / ethanol / 0 - 20 °C 4: 64 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 5: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With sodium tetrahydroborate, lithium aluminium tetrahydride, dipyridinium dichromate, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, ethanol, dichloromethane, N,N-dimethyl-formamide Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360 View in Reaxys Reaction Steps: 3 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 64 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 3: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With lithium aluminium tetrahydride, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, dichloromethane Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360 View in Reaxys Reaction Steps: 2 1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C 1.2: tetrahydrofuran; hexane / -78 °C 2.1: 83 percent / CsF; H2O / dimethylformamide / 48 h / 92 °C With n-butyllithium, potassium tert-butylate, water, cesium fluoride in tetrahydrofuran, hexane, N,N-dimethyl-formamide, 1.1: Metallation / 1.2: Addition / 2.1: Elimination Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Tokitoh, Norihiro; Okazaki, Renji; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 209 - 219 View in Reaxys Reaction Steps: 2 1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C 1.2: tetrahydrofuran; hexane / -78 °C 2.1: CsF; H2O / dimethylformamide / 48 h / 75 - 100 °C With n-butyllithium, potassium tert-butylate, water, cesium fluoride in tetrahydrofuran, hexane, N,N-dimethyl-formamide, 1.1: Metallation / 1.2: Addition / 2.1: Elimination Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Tokitoh, Norihiro; Okazaki, Renji; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 209 - 219 View in Reaxys

H O

HI, I2

Rx-ID: 16481576 View in Reaxys 55/276 Yield

Conditions & References Reaction Steps: 3

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1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 64 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 3: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With lithium aluminium tetrahydride, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, dichloromethane Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360 View in Reaxys Reaction Steps: 3 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 88 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 3: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With lithium aluminium tetrahydride, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, dichloromethane Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360 View in Reaxys Reaction Steps: 5 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 94 percent / PDC / dimethylformamide / Ambient temperature 3: 47 percent / NaBH4 / ethanol / 0 - 20 °C 4: 64 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 5: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With sodium tetrahydroborate, lithium aluminium tetrahydride, dipyridinium dichromate, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, ethanol, dichloromethane, N,N-dimethyl-formamide Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360 View in Reaxys Reaction Steps: 3 1: 1.) n-BuLi / 1.) THF, hexane, 0 deg C, 30 min, 2.) THF, hexane, -78 deg C to rt, 2 h 2: 64 percent / CeCl3, LiAlH4 / tetrahydrofuran / 2 h / Ambient temperature 3: PCl3, Et3N / CH2Cl2 / 3 h / 0 °C With lithium aluminium tetrahydride, n-butyllithium, cerium(III) chloride, triethylamine, phosphorus trichoride in tetrahydrofuran, dichloromethane Lawrence, Nicholas J.; Muhammad, Faiz; Tetrahedron; vol. 54; nb. 50; (1998); p. 15345 - 15360 View in Reaxys Reaction Steps: 2 1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / 0.08 h / -78 °C 1.2: tetrahydrofuran; hexane / -78 °C 2.1: CsF; H2O / dimethylformamide / 48 h / 75 - 100 °C With n-butyllithium, potassium tert-butylate, water, cesium fluoride in tetrahydrofuran, hexane, N,N-dimethyl-formamide, 1.1: Metallation / 1.2: Addition / 2.1: Elimination Kawashima, Takayuki; Ishii, Takafumi; Inamoto, Naoki; Tokitoh, Norihiro; Okazaki, Renji; Bulletin of the Chemical Society of Japan; vol. 71; nb. 1; (1998); p. 209 - 219 View in Reaxys

O O

Rx-ID: 12508470 View in Reaxys 56/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction

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Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys Reaction Steps: 3 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating 3: 0.03 h / 25 °C / UV-irradiation With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys Reaction Steps: 3 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating 3: hexane / 25 °C / UV-irradiation With toluene-4-sulfonic acid in diethyl ether, hexane, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys

Rx-ID: 13524695 View in Reaxys 57/276 Yield

Conditions & References Reaction Steps: 2 1.1: NaH / dimethylformamide / 0 - 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.67 h / 0 - 20 °C 2.2: 13.2 g / tetrahydrofuran; hexane / 4 h / 0 - 20 °C With n-butyllithium, sodium hydride in tetrahydrofuran, hexane, N,N-dimethyl-formamide Malamas, Michael S.; Manas, Eric S.; McDevitt, Robert E.; Gunawan, Iwan; Xu, Zhang B.; Collini, Michael D.; Miller, Chris P.; Dinh, Tam; Henderson, Ruth A.; Keith Jr., James C.; Harris, Heather A.; Journal of Medicinal Chemistry; vol. 47; nb. 21; (2004); p. 5021 - 5040 View in Reaxys

Br O

Rx-ID: 14740633 View in Reaxys 58/276 Yield

Conditions & References Reaction Steps: 2 1: 76 percent / diethyl ether / 1 h / 20 °C 2: 78 percent / sodium hydrogensulfate; p-hydroquinone; 4-tert-butylcatechol / diethyl ether / 3 h / 200 °C With sodium hydrogen sulphate, 3,4-dihydroxy-1-tert-butylbenzene, hydroquinone in diethyl ether Zaidlewicz, Marek; Wolan, Andrzej; Journal of Organometallic Chemistry; vol. 657; nb. 1-2; (2002); p. 129 - 135 View in Reaxys Reaction Steps: 2 1: 1) t-BuOK / 1) THF, ca. 20 deg C, 2 h, 2) THF, 20 min 2: diethyl ether / 1 h / 0 °C With potassium tert-butylate in diethyl ether Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys Reaction Steps: 2 1: 1) t-BuOK / 1) THF, ca. 20 deg C, 2 h, 2) THF, 20 min 2: tetrahydrofuran / 0.25 h / -78 °C

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With potassium tert-butylate in tetrahydrofuran Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys Reaction Steps: 2 1: 1) t-BuOK / 1) THF, ca. 20 deg C, 2 h, 2) THF, 20 min 2: tetrahydrofuran / 1 h / -70 °C With potassium tert-butylate in tetrahydrofuran Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys

Rx-ID: 28662285 View in Reaxys 59/276 Yield

Conditions & References With boron trifluoride diethyl etherate in hexane, Time= 18h, T= 20 °C McGuigan, Christopher; Bidet, Olivier; Derudas, Marco; Andrei, Graciela; Snoeck, Robert; Balzarini, Jan; Bioorganic and Medicinal Chemistry; vol. 17; nb. 8; (2009); p. 3025 - 3027 View in Reaxys

(halomethyl)(methyl)(triphenyl)-λ5-phosphane

O O

Rx-ID: 29083862 View in Reaxys 60/276 Yield

Conditions & References With potassium carbonate in 1,4-dioxane, Inert atmosphere, Reflux Fan, Jinmin; Gao, Linfeng; Wang, Zhiyong; Chemical Communications; nb. 33; (2009); p. 5021 - 5023 View in Reaxys O

Rx-ID: 32834487 View in Reaxys 61/276 Yield

Conditions & References Reaction Steps: 3 1.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 1.2: 15 h / -78 - 20 °C / Inert atmosphere 2.1: oxygen / dimethyl sulfoxide / 24 h / 20 °C / 1500.15 Torr / pH 6 / aq. buffer; Enzymatic reaction 3.1: potassium tert-butylate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere 3.2: 15 h / -78 - 20 °C / Inert atmosphere With potassium tert-butylate, oxygen in tetrahydrofuran, dimethyl sulfoxide, 1.2: Wittig reaction / 3.2: Wittig reaction Paul, Caroline E.; Rajagopalan, Aashrita; Lavandera, Ivan; Gotor-Fernandez, Vicente; Kroutil, Wolfgang; Gotor, Vicente; Chemical Communications; vol. 48; nb. 27; (2012); p. 3303 - 3305 View in Reaxys

Rx-ID: 32834538 View in Reaxys 62/276

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Yield

Rx-ID: 32834544 View in Reaxys 63/276 Yield

Rx-ID: 33133478 View in Reaxys 64/276 Yield

Conditions & References Reaction Steps: 3 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C / Inert atmosphere With n-butyllithium, pyridinium chlorochromate in tetrahydrofuran, hexane, dichloromethane Shao, Yutian; Yang, Chao; Gui, Weijun; Liu, Yang; Xia, Wujiong; Chemical Communications; vol. 48; nb. 29; (2012); p. 3560 - 3562 View in Reaxys

Rx-ID: 35784578 View in Reaxys 65/276 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C / |Inert atmosphere 1.2: 0 - 20 °C / |Inert atmosphere 2.1: 4-methyl-morpholine / acetonitrile / 20 °C / |Inert atmosphere With 4-methyl-morpholine, n-butyllithium in tetrahydrofuran, acetonitrile

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Zhu, Jian-Bo; Wang, Peng; Liao, Saihu; Tang, Yong; Organic Letters; vol. 15; nb. 12; (2013); p. 3054 - 3057 View in Reaxys Br

Br O

Rx-ID: 37363807 View in Reaxys 66/276 Yield

Conditions & References Reaction Steps: 2 1: toluene; diethyl ether / 16 h / 0 °C 2: silica gel / 1,4-dioxane / |Microwave irradiation With silica gel in 1,4-dioxane, diethyl ether, toluene Neve, Juliette E.; Wijesekera, Hasanthi P.; Duffy, Sandra; Jenkins, Ian D.; Ripper, Justin A.; Teague, Simon J.; Campitelli, Marc; Garavelas, Agatha; Nikolakopoulos, George; Le, Phuc V.; De A. Leone, Priscila; Pham, Ngoc B.; Shelton, Philip; Fraser, Neil; Carroll, Anthony R.; Avery, Vicky M.; McCrae, Christopher; Williams, Nicola; Quinn, Ronald J.; Journal of Medicinal Chemistry; vol. 57; nb. 4; (2014); p. 1252 - 1275 View in Reaxys

Cl Cl

O O

Rx-ID: 37363809 View in Reaxys 67/276 Yield

Rx-ID: 42720565 View in Reaxys 68/276 Yield

Conditions & References Reaction Steps: 2 1: palladium diacetate; triphenylphosphine; caesium carbonate / water; tetrahydrofuran / 4 h / 70 °C / |Inert atmosphere; |Sealed tube 2: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; trimethylsilylazide / dichloromethane / 1 h / 20 °C / |Inert atmosphere; |Irradiation With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate, trimethylsilylazide, palladium diacetate, caesium carbonate, triphenylphosphine in tetrahydrofuran, dichloromethane, water Jarrige, Lucie; Carboni, Aude; Dagousset, Guillaume; Levitre, Guillaume; Magnier, Emmanuel; Masson, Géraldine; Organic Letters; vol. 18; nb. 12; (2016); p. 2906 - 2909 View in Reaxys

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O O

Rx-ID: 44289539 View in Reaxys 69/276 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / 0 °C 1.2: 12 h / 0 - 20 °C 2.1: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 12 h / 20 °C With dichloro bis(acetonitrile) palladium(II), n-butyllithium in tetrahydrofuran, dichloromethane Colomer, Ignacio; Barcelos, Rosimeire Coura; Christensen, Kirsten E.; Donohoe, Timothy J.; Organic Letters; vol. 18; nb. 22; (2016); p. 5880 - 5883 View in Reaxys F

O O

Rx-ID: 44289541 View in Reaxys 70/276 Yield

O O

Rx-ID: 44289543 View in Reaxys 71/276 Yield

Rx-ID: 44289545 View in Reaxys 72/276 Yield

Conditions & References Reaction Steps: 2 1.1: potassium tert-butylate / diethyl ether / 0.5 h / 0 °C

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1.2: 12 h / 0 - 20 °C 2.1: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 12 h / 20 °C With dichloro bis(acetonitrile) palladium(II), potassium tert-butylate in diethyl ether, dichloromethane Colomer, Ignacio; Barcelos, Rosimeire Coura; Christensen, Kirsten E.; Donohoe, Timothy J.; Organic Letters; vol. 18; nb. 22; (2016); p. 5880 - 5883 View in Reaxys Br

O O

Rx-ID: 44289553 View in Reaxys 73/276 Yield

F O

Rx-ID: 45966563 View in Reaxys 74/276 Yield

Conditions & References Reaction Steps: 2 1.1: tetrahydrofuran / 0 - 20 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: toluene-4-sulfonic acid / benzene / 3 h / Inert atmosphere; Reflux; Dean-Stark With toluene-4-sulfonic acid in tetrahydrofuran, benzene Daniel, Paige E.; Weber, Alexandria E.; Malcolmson, Steven J.; Organic Letters; vol. 19; nb. 13; (2017); p. 3490 3493 View in Reaxys

N O

Rx-ID: 45966583 View in Reaxys 75/276 Yield

O Z

Rx-ID: 12502404 View in Reaxys 76/276

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Yield

Conditions & References Reaction Steps: 3 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating 3: 0.17 h / 25 °C / UV-irradiation With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys Reaction Steps: 2 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys

indenyl magnesium bromide

Rx-ID: 12507960 View in Reaxys 77/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys Reaction Steps: 3 1: diethyl ether 2: p-toluenesulfonic acid / benzene / Heating 3: 0.17 h / 25 °C / UV-irradiation With toluene-4-sulfonic acid in diethyl ether, benzene, 1: Grignard reaction Roberts, Jeffrey C.; Pincock, James A.; Journal of Organic Chemistry; vol. 71; nb. 4; (2006); p. 1480 - 1492 View in Reaxys

Rx-ID: 12510958 View in Reaxys 78/276 Yield

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dimer(ic) phenylcyclopropane O

Rx-ID: 19263732 View in Reaxys 79/276 Yield

Conditions & References Reaction Steps: 3 1: 1.) Mg / 1.) ether, reflux, 2 h; 2.) ether, 12 h, room temp. 2: 87 percent / potassium hydrogen sulfate, phosphorus pentoxide, 4-tert-butylcatechol / 230 °C 3: 1.) Mg / 1.) THF, 60 deg C, 40 min; 2.) ether, -78 to 5 deg C, overnight With P2O5, potassium hydrogensulfate, 3,4-dihydroxy-1-tert-butylbenzene, magnesium Padwa, Albert; Rieker, William F.; Rosenthal, Robert J.; Journal of the American Chemical Society; vol. 107; nb. 6; (1985); p. 1710 - 1717 View in Reaxys Br

Br E

Rx-ID: 19263735 View in Reaxys 80/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) Mg / 1.) ether, reflux, 2 h; 2.) ether, 12 h, room temp. 2: 87 percent / potassium hydrogen sulfate, phosphorus pentoxide, 4-tert-butylcatechol / 230 °C With P2O5, potassium hydrogensulfate, 3,4-dihydroxy-1-tert-butylbenzene, magnesium Padwa, Albert; Rieker, William F.; Rosenthal, Robert J.; Journal of the American Chemical Society; vol. 107; nb. 6; (1985); p. 1710 - 1717 View in Reaxys

HO E O

Rx-ID: 19879126 View in Reaxys 81/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / 2.5 h / Heating 2: CH3COOH / 0.17 h / Heating With acetic acid in diethyl ether Nishinaga, Akira; Iwasaki, Hitoshi; Shimizu, Tadashi; Toyoda, Yasushi; Matsuura, Teru; Journal of Organic Chemistry; vol. 51; nb. 12; (1986); p. 2257 - 2266 View in Reaxys Reaction Steps: 5 1: diethyl ether / 2.5 h / Heating 2: CH3COOH / 0.17 h / Heating 3: 80 percent Spectr. / t-BuOK, O2 / 2-methyl-propan-2-ol; hexane / 0.5 h / 0 °C 4: diethyl ether / 2.5 h / Heating 5: CH3COOH / 0.17 h / Heating With potassium tert-butylate, oxygen, acetic acid in diethyl ether, hexane, tert-butyl alcohol Nishinaga, Akira; Iwasaki, Hitoshi; Shimizu, Tadashi; Toyoda, Yasushi; Matsuura, Teru; Journal of Organic Chemistry; vol. 51; nb. 12; (1986); p. 2257 - 2266 View in Reaxys

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HO O

O OH

Rx-ID: 22107758 View in Reaxys 82/276 Yield

Conditions & References Reaction Steps: 4 1: aqueous HCl; toluene; amalgamated zinc 2: aqueous NaOH; acetone 3: 200 - 230 °C 4: KOH; diethylene glycol / 150 - 170 °C With hydrogenchloride, potassium hydroxide, sodium hydroxide, amalgamated zinc, acetone, toluene, diethylene glycol Fletcher; Tarbell; Journal of the American Chemical Society; vol. 65; (1943); p. 1431 View in Reaxys

HO O

O O

Rx-ID: 22107759 View in Reaxys 83/276 Yield

Conditions & References Reaction Steps: 5 1: aqueous HCl; toluene; amalgamated zinc 2: aqueous NaOH; acetone 3: 200 - 230 °C 4: diluted aqueous NaOH 5: KOH; diethylene glycol / 175 - 185 °C With hydrogenchloride, potassium hydroxide, sodium hydroxide, amalgamated zinc, acetone, toluene, diethylene glycol Fletcher; Tarbell; Journal of the American Chemical Society; vol. 65; (1943); p. 1431 View in Reaxys

Br–

O P+

P O

Rx-ID: 2701621 View in Reaxys 84/276 Yield

F B

B–

K+

Rx-ID: 12280445 View in Reaxys 85/276 Yield

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Molander, Gary A.; Figueroa, Ruth; Journal of Organic Chemistry; vol. 71; nb. 16; (2006); p. 6135 - 6140 View in Reaxys F

B–

B HO

K+

Rx-ID: 12280446 View in Reaxys 86/276 Yield

Conditions & References Reaction Steps: 2 1: 80 percent / KHF2 / methanol; H2O / 0.5 h 2: dimethylformamide / 3 h / -78 - 20 °C With KHF2 in methanol, water, N,N-dimethyl-formamide, 2: Wittig reaction Molander, Gary A.; Figueroa, Ruth; Journal of Organic Chemistry; vol. 71; nb. 16; (2006); p. 6135 - 6140 View in Reaxys

indenyl magnesium bromide

Rx-ID: 12507964 View in Reaxys 87/276 Yield

Rx-ID: 12510957 View in Reaxys 88/276 Yield

O O

O E O

O O

Rx-ID: 13131693 View in Reaxys 89/276 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium / diethyl ether / 2 h 1.2: 78 percent / diethyl ether; toluene / 20 °C 2.1: 68 percent / silica gel / dioxane / 0.05 h / microwave irradiation With silica gel, magnesium in 1,4-dioxane, diethyl ether, 1.2: Grignard reaction Sharma, Anuj; Joshi, Bhupendra P.; Sinha, Arun K.; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2231 - 2235 View in Reaxys

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Reaction Steps: 2 1.1: Mg; I2 / diethyl ether 1.2: 30 percent / diethyl ether / 0.5 h / Heating 2.1: 95 percent / AcONa; Ac2O / 3 h / Heating With iodine, sodium acetate, acetic anhydride, magnesium in diethyl ether, 1.1: Metallation / 1.2: Grignard reaction / 2.1: Dehydration Diaz, Francisco; Contreras, Leticia; Flores, Rosa; Tamariz, Joaquin; Labarrios, Fernando; et al.; Organic Preparations and Procedures International; vol. 23; nb. 2; (1991); p. 133 - 138 View in Reaxys

O Si

O O

OH R(a)-isomer

O R(a)-isomer

Rx-ID: 13852045 View in Reaxys 90/276 Yield

Conditions & References Reaction Steps: 2 1.1: 98 percent / DMAP; imidazole / CH2Cl2 / 2 h / 20 °C 2.1: KHMDS / tetrahydrofuran; toluene / 0.5 h / 0 °C 2.2: tetrahydrofuran; toluene / -78 - 20 °C With 1H-imidazole, 4-(N,N-dimethlyamino)pyridine, potassium hexamethylsilazane in tetrahydrofuran, dichloromethane, toluene, 2.1: Wittig reaction Molander, Gary A.; George, Kelly M.; Monovich, Lauren G.; Journal of Organic Chemistry; vol. 68; nb. 25; (2003); p. 9533 - 9540 View in Reaxys

O O

Si O

O O

O O O

OH R(a)-isomer

O R(a)-isomer

Rx-ID: 13852046 View in Reaxys 91/276 Yield

O O

(E/Z)-crotylstannane(1-)*Et4N(1+)

Rx-ID: 15596033 View in Reaxys 92/276

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Yield

Conditions & References Reaction Steps: 2 1.1: 74 percent / t-BuOK / tetrahydrofuran / 1 h / -78 °C 2.1: tert-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: tetrahydrofuran; hexane / -78 - 20 °C With potassium tert-butylate, tert.-butyl lithium in tetrahydrofuran, hexane, 1.1: Wittig reaction Vassilikogiannakis; Hatzimarinaki; Orfanopoulos; Journal of Organic Chemistry; vol. 65; nb. 24; (2000); p. 8180 8187 View in Reaxys

Rx-ID: 16964631 View in Reaxys 93/276 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran; diethyl ether / 2 h / Heating 2: conc. H3PO4 / 0.75 h / Heating With phosphoric acid in tetrahydrofuran, diethyl ether Meade, Eric A.; Sznaidman, Marcos; Pollard, Gerald T.; Beauchamp, Lilia M.; Howard, James L.; European Journal of Medicinal Chemistry; vol. 33; nb. 5; (1998); p. 363 - 374 View in Reaxys

Rx-ID: 16964632 View in Reaxys 94/276 Yield

Conditions & References Reaction Steps: 3 1: tetrahydrofuran; diethyl ether / 2 h / Heating 2: conc. H3PO4 / 0.75 h / Heating 3: 84 percent / dimethylformamide / 6 h / Heating With phosphoric acid in tetrahydrofuran, diethyl ether, N,N-dimethyl-formamide Meade, Eric A.; Sznaidman, Marcos; Pollard, Gerald T.; Beauchamp, Lilia M.; Howard, James L.; European Journal of Medicinal Chemistry; vol. 33; nb. 5; (1998); p. 363 - 374 View in Reaxys

4-dimethylamino-benzyl magnesium chloride Rx-ID: 17166719 View in Reaxys 95/276

Yield

Conditions & References Reaction Steps: 2 1: 1.) Mg / 1.) Et2O, 0 deg C, 2.) Et2O, 0 deg C -> rt 2: 90 percent / p-TsOH*H2O / benzene / 0.5 h / Heating With toluene-4-sulfonic acid, magnesium in benzene Kulasegaram, Sanjitha; Kulawiec, Robert J.; Journal of Organic Chemistry; vol. 62; nb. 19; (1997); p. 6547 - 6561 View in Reaxys

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O O

Rx-ID: 19152992 View in Reaxys 96/276 Yield

Conditions & References Reaction Steps: 6 1: 95 percent / p-TsOH / benzene / 2 h / Heating 2: 1) n-BuLi / 1) ether, hexane, -78 deg C, 1 h, 2a) -78 deg C to RT, 2b) RT, 2 h 3: SOCl2, pyridine / diethyl ether / 0.5 h / -78 °C 4: LiAlH4 / tetrahydrofuran / 25 °C 5: aq. HCl / ethyl acetate / 1 h / Ambient temperature 6: NaH / tetrahydrofuran; dimethylsulfoxide With pyridine, hydrogenchloride, lithium aluminium tetrahydride, n-butyllithium, thionyl chloride, sodium hydride, toluene-4-sulfonic acid in tetrahydrofuran, diethyl ether, dimethyl sulfoxide, ethyl acetate, benzene Reitz, Allen; Avery, Mitchell A.; Verlander, Michael S.; Goodman, Murray; Journal of Organic Chemistry; vol. 46; nb. 24; (1981); p. 4859 - 4863 View in Reaxys

O E O

O O

Rx-ID: 19152994 View in Reaxys 97/276 Yield

Conditions & References Reaction Steps: 4 1: 95 percent / p-TsOH / benzene / 2 h / Heating 2: 1) n-BuLi / 1) ether, hexane, -78 deg C, 1 h, 2a) -78 deg C to RT, 2b) RT, 2 h 3: SOCl2, pyridine / diethyl ether / 0.5 h / -78 °C 4: LiAlH4 / tetrahydrofuran / 25 °C With pyridine, lithium aluminium tetrahydride, n-butyllithium, thionyl chloride, toluene-4-sulfonic acid in tetrahydrofuran, diethyl ether, benzene Reitz, Allen; Avery, Mitchell A.; Verlander, Michael S.; Goodman, Murray; Journal of Organic Chemistry; vol. 46; nb. 24; (1981); p. 4859 - 4863 View in Reaxys

HO O O

HN O

Rx-ID: 19152995 View in Reaxys 98/276 Yield

Conditions & References Reaction Steps: 7 1: 95 percent / p-TsOH / benzene / 2 h / Heating

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2: 1) n-BuLi / 1) ether, hexane, -78 deg C, 1 h, 2a) -78 deg C to RT, 2b) RT, 2 h 3: SOCl2, pyridine / diethyl ether / 0.5 h / -78 °C 4: LiAlH4 / tetrahydrofuran / 25 °C 5: aq. HCl / ethyl acetate / 1 h / Ambient temperature 6: NaH / tetrahydrofuran; dimethylsulfoxide 7: 30 percent / ethanol / Heating With pyridine, hydrogenchloride, lithium aluminium tetrahydride, n-butyllithium, thionyl chloride, sodium hydride, toluene-4-sulfonic acid in tetrahydrofuran, diethyl ether, ethanol, dimethyl sulfoxide, ethyl acetate, benzene Reitz, Allen; Avery, Mitchell A.; Verlander, Michael S.; Goodman, Murray; Journal of Organic Chemistry; vol. 46; nb. 24; (1981); p. 4859 - 4863 View in Reaxys

Rx-ID: 21164844 View in Reaxys 99/276 Yield

Conditions & References Reaction Steps: 2 1: 85 percent / diethyl ether / 3 h / Heating 2: conc. aq. HCl / acetic acid / 0.5 h / Heating With hydrogenchloride in diethyl ether, acetic acid Tashiro, Masashi; Yamato, Takehiko; Journal of Organic Chemistry; vol. 48; nb. 9; (1983); p. 1461 - 1468 View in Reaxys

F O

Rx-ID: 22537015 View in Reaxys 100/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / Heating 2: HCO2H With formic acid in diethyl ether Buu-Hoi,N.P. et al.; Journal of Organic Chemistry; vol. 27; (1962); p. 2669 - 2670 View in Reaxys

O O

N O

Rx-ID: 34132457 View in Reaxys 101/276 Yield

Conditions & References Reaction Steps: 3 1: potassium carbonate 2: nitric acid / dichloromethane / 12 h / -10 - 10 °C With nitric acid, potassium carbonate in dichloromethane, 3: |Wittig Olefination Knapkiewicz, Pawel; Skowerski, Krzysztof; Jaskolska, Dagmara E.; Barbasiewicz, Michal; Olszewski, Tomasz K.; Organic Process Research and Development; vol. 16; nb. 8; (2012); p. 1430 - 1435 View in Reaxys Reaction Steps: 3 1: potassium carbonate 2: nitric acid / dichloromethane / 2 h / 10 °C With nitric acid, potassium carbonate in dichloromethane, 3: |Wittig Olefination

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Knapkiewicz, Pawel; Skowerski, Krzysztof; Jaskolska, Dagmara E.; Barbasiewicz, Michal; Olszewski, Tomasz K.; Organic Process Research and Development; vol. 16; nb. 8; (2012); p. 1430 - 1435 View in Reaxys Reaction Steps: 3 1: nitric acid; acetic acid 2: potassium carbonate; caesium carbonate With nitric acid, potassium carbonate, caesium carbonate, acetic acid, 3: |Wittig Olefination Knapkiewicz, Pawel; Skowerski, Krzysztof; Jaskolska, Dagmara E.; Barbasiewicz, Michal; Olszewski, Tomasz K.; Organic Process Research and Development; vol. 16; nb. 8; (2012); p. 1430 - 1435 View in Reaxys

Br O

Br E

Rx-ID: 44511188 View in Reaxys 102/276 Yield

Conditions & References With chromium dichloride in tetrahydrofuran, Inert atmosphere Rivero-Crespo, Miguel A.; Leyva-Pérez, Antonio; Corma, Avelino; Chemistry - A European Journal; vol. 23; nb. 7; (2017); p. 1702 - 1708 View in Reaxys

Rx-ID: 12198693 View in Reaxys 103/276 Yield

Conditions & References Reaction Steps: 2 1: 100 percent / [RuClH(CO)(PPh3)3] / toluene / 4 h / 80 - 90 °C 2: tetrahydrofuran With carbonylchlorohydridetris(triphenylphosphine) ruthenium(II) in tetrahydrofuran, toluene Coyanis, E. Mabel; Panayides, Jenny-Lee; Fernandes, Manuel A.; de Koning, Charles B.; van Otterlo, Willem A.L.; Journal of Organometallic Chemistry; vol. 691; nb. 24-25; (2006); p. 5222 - 5239 View in Reaxys Reaction Steps: 2 1: 49 percent / tetrahydrofuran / -20 - 0 °C 2: tBuOK / dimethylformamide / 0.25 h / 20 °C With potassium tert-butylate in tetrahydrofuran, N,N-dimethyl-formamide Coyanis, E. Mabel; Panayides, Jenny-Lee; Fernandes, Manuel A.; de Koning, Charles B.; van Otterlo, Willem A.L.; Journal of Organometallic Chemistry; vol. 691; nb. 24-25; (2006); p. 5222 - 5239 View in Reaxys O

OH O

Rx-ID: 12198694 View in Reaxys 104/276 Yield

Conditions & References Reaction Steps: 2 1: 100 percent / [RuClH(CO)(PPh3)3] / toluene / 4 h / 80 - 90 °C

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2: tetrahydrofuran With carbonylchlorohydridetris(triphenylphosphine) ruthenium(II) in tetrahydrofuran, toluene Coyanis, E. Mabel; Panayides, Jenny-Lee; Fernandes, Manuel A.; de Koning, Charles B.; van Otterlo, Willem A.L.; Journal of Organometallic Chemistry; vol. 691; nb. 24-25; (2006); p. 5222 - 5239 View in Reaxys Reaction Steps: 2 1: 49 percent / tetrahydrofuran / -20 - 0 °C 2: tBuOK / dimethylformamide / 0.25 h / 20 °C With potassium tert-butylate in tetrahydrofuran, N,N-dimethyl-formamide Coyanis, E. Mabel; Panayides, Jenny-Lee; Fernandes, Manuel A.; de Koning, Charles B.; van Otterlo, Willem A.L.; Journal of Organometallic Chemistry; vol. 691; nb. 24-25; (2006); p. 5222 - 5239 View in Reaxys

XCH2(CO)CH3 X = halogen

Rx-ID: 15305278 View in Reaxys 105/276 Yield

Conditions & References Reaction Steps: 4 1: 90 percent / hydrazine monohydrate; K2CO3 / triethylene glycol / 4.5 h / 200 °C / Heating 2: 85 percent / K2CO3 / acetone / 12 h 3: 76 percent / 4 h / 180 °C 4: 91 percent / potassium tert-butanolate / dimethylsulfoxide / 2 h / 110 °C With potassium tert-butylate, potassium carbonate, hydrazine hydrate in dimethyl sulfoxide, acetone, 1,2-bis-(2-hydroxyethoxy)-ethane Bertrand, Franck; Basketter, David A.; Roberts, David W.; Lepoittevin, Jean-Pierre; Chemical Research in Toxicology; vol. 10; nb. 3; (1997); p. 335 - 343 View in Reaxys

O O

Rx-ID: 22491478 View in Reaxys 106/276 Yield

Conditions & References Reaction Steps: 3 1: (i) Et2O, (ii) CrO3, aq. H2SO4, acetone 2: Br2 / CHCl3 3: (i) NaOEt, EtOH, (ii) /BRN= 1988473/ With bromine in chloroform Barata,L.E.S. et al.; Phytochemistry (Elsevier); vol. 17; (1978); p. 783 - 786 View in Reaxys

Rx-ID: 31046193 View in Reaxys 107/276 Yield

Conditions & References Reaction Steps: 3 1: sodium hydride / tetrahydrofuran 2: potassium carbonate / tetrahydrofuran

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3: hydrogenchloride; water / methanol / 20 °C With hydrogenchloride, water, sodium hydride, potassium carbonate in tetrahydrofuran, methanol, 2: Wittig reaction Xia, Yamu; Chang, Liang; Ding, Yining; Jiao, Bin; Mendeleev Communications; vol. 20; nb. 3; (2010); p. 151 152 View in Reaxys Reaction Steps: 3 1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran / 0 °C 3: hydrogenchloride / methanol / 8 h / 20 °C With hydrogenchloride, n-butyllithium, sodium hydride in tetrahydrofuran, methanol, 2: Wittig reaction Xia, Yamu; Wang, Wei; Chemical Papers; vol. 64; nb. 5; (2010); p. 630 - 636 View in Reaxys

O O

Rx-ID: 31046195 View in Reaxys 108/276 Yield

Conditions & References Reaction Steps: 2 1: sodium hydride / tetrahydrofuran 2: potassium carbonate / tetrahydrofuran With sodium hydride, potassium carbonate in tetrahydrofuran, 2: Wittig reaction Xia, Yamu; Chang, Liang; Ding, Yining; Jiao, Bin; Mendeleev Communications; vol. 20; nb. 3; (2010); p. 151 152 View in Reaxys Reaction Steps: 2 1: sodium hydride / tetrahydrofuran / 20 °C / Inert atmosphere 2: n-butyllithium / tetrahydrofuran / 0 °C With n-butyllithium, sodium hydride in tetrahydrofuran, 2: Wittig reaction Xia, Yamu; Wang, Wei; Chemical Papers; vol. 64; nb. 5; (2010); p. 630 - 636 View in Reaxys

O O

Rx-ID: 33379003 View in Reaxys 109/276 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate / N,N-dimethyl-formamide / 42 h / 45 °C 2: potassium 2-methyl-2-butoxide / tetrahydrofuran; toluene With potassium 2-methyl-2-butoxide, potassium carbonate in tetrahydrofuran, N,N-dimethyl-formamide, toluene, 2: Wittig reaction Grudzien, Krzysztof; Malinska, Maura; Barbasiewicz, Michal; Organometallics; vol. 31; nb. 9; (2012); p. 3636 3646 View in Reaxys

O HO

Rx-ID: 38875751 View in Reaxys 110/276

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Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran / 1 h / 0 °C 2: triethylamine; oxalyl dichloride / dichloromethane; dimethyl sulfoxide; 1,4-dioxane / 1 h / -78 - 20 °C / |Inert atmosphere With oxalyl dichloride, triethylamine in tetrahydrofuran, 1,4-dioxane, dichloromethane, dimethyl sulfoxide, 2: |Swern Oxidation Chanda, Tanmoy; Chowdhury, Sushobhan; Koley, Suvajit; Anand, Namrata; Singh, Maya Shankar; Organic and Biomolecular Chemistry; vol. 12; nb. 45; (2014); p. 9216 - 9222 View in Reaxys

Rx-ID: 38875753 View in Reaxys 111/276 Yield

O O

O OH

Rx-ID: 12198699 View in Reaxys 112/276 Yield

Conditions & References Reaction Steps: 2 1: 100 percent / [RuClH(CO)(PPh3)3] / toluene / 4 h / 80 - 90 °C 2: 85 percent / tetrahydrofuran / -60 - 20 °C With carbonylchlorohydridetris(triphenylphosphine) ruthenium(II) in tetrahydrofuran, toluene Coyanis, E. Mabel; Panayides, Jenny-Lee; Fernandes, Manuel A.; de Koning, Charles B.; van Otterlo, Willem A.L.; Journal of Organometallic Chemistry; vol. 691; nb. 24-25; (2006); p. 5222 - 5239 View in Reaxys

5-fluoro-2-trifluoromethylbenzyl halide

O OH

Rx-ID: 12699650 View in Reaxys 113/276 Yield

Conditions & References Reaction Steps: 4 1: 80 percent / zinc amalgam; HCl / ethanol / 3 h / Heating 2: 95 percent / K2CO3 / acetone / 6 h / Heating 3: 90 percent / 24 h / 180 °C 4: 95 percent / KOH / methanol / 10 h / Heating With hydrogenchloride, potassium hydroxide, Zn–Hg amalgam, potassium carbonate in methanol, ethanol, acetone, 1: Clemmensen reduction / 3: Claisen rearrangement

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Srikrishna; Satyanarayana; Tetrahedron; vol. 62; nb. 12; (2006); p. 2892 - 2900 View in Reaxys

5-fluoro-2-trifluoromethylbenzyl halide

O O

Rx-ID: 12699651 View in Reaxys 114/276 Yield

Conditions & References Reaction Steps: 5 1: 80 percent / zinc amalgam; HCl / ethanol / 3 h / Heating 2: 95 percent / K2CO3 / acetone / 6 h / Heating 3: 90 percent / 24 h / 180 °C 4: 95 percent / KOH / methanol / 10 h / Heating 5: 96 percent / sodium hydroxyde / H2O / 1 h / Heating With hydrogenchloride, potassium hydroxide, sodium hydroxide, Zn–Hg amalgam, potassium carbonate in methanol, ethanol, water, acetone, 1: Clemmensen reduction / 3: Claisen rearrangement Srikrishna; Satyanarayana; Tetrahedron; vol. 62; nb. 12; (2006); p. 2892 - 2900 View in Reaxys

Z O

Rx-ID: 13131692 View in Reaxys 115/276 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium / diethyl ether / 2 h 1.2: 78 percent / diethyl ether; toluene / 20 °C 2.1: silica gel / dioxane / 0.05 h / microwave irradiation With silica gel, magnesium in 1,4-dioxane, diethyl ether, 1.2: Grignard reaction Sharma, Anuj; Joshi, Bhupendra P.; Sinha, Arun K.; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2231 - 2235 View in Reaxys

α-hydrazino-phenylacetic acid

Rx-ID: 13138294 View in Reaxys 116/276 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium / diethyl ether / 2 h 1.2: 78 percent / diethyl ether; toluene / 20 °C 2.1: 67 percent / silica gel / dioxane / 0.05 h / microwave irradiation With silica gel, magnesium in 1,4-dioxane, diethyl ether, 1.2: Grignard reaction Sharma, Anuj; Joshi, Bhupendra P.; Sinha, Arun K.; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2231 - 2235 View in Reaxys

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O O

polymer-PPh2 (1+)-CH2-Ph*Br(1-)

Rx-ID: 13138652 View in Reaxys 117/276 Yield

Conditions & References Reaction Steps: 2 1.1: magnesium / diethyl ether / 2 h 1.2: 80 percent / diethyl ether; toluene / 20 °C 2.1: 72 percent / silica gel / dioxane / 0.05 h / microwave irradiation With silica gel, magnesium in 1,4-dioxane, diethyl ether, 1.2: Grignard reaction Sharma, Anuj; Joshi, Bhupendra P.; Sinha, Arun K.; Bulletin of the Chemical Society of Japan; vol. 77; nb. 12; (2004); p. 2231 - 2235 View in Reaxys Br

Br E

Rx-ID: 13864060 View in Reaxys 118/276 Yield

Conditions & References Reaction Steps: 2 1.1: NaH / dimethylsulfoxide; tetrahydrofuran / 60 °C 1.2: 90 percent / 2 h / 60 °C 2.1: 99 percent / thiophenol; AIBN / toluene / 2 h / 80 °C With 2,2'-azobis(isobutyronitrile), sodium hydride, thiophenol in tetrahydrofuran, dimethyl sulfoxide, toluene Bianchi, Dario A.; Cipulli, Marcos A.; Kaufman, Teodoro S.; European Journal of Organic Chemistry; nb. 24; (2003); p. 4731 - 4736 View in Reaxys Br O

E O

Rx-ID: 13871785 View in Reaxys 119/276 Yield

Conditions & References Reaction Steps: 3 1.1: 93 percent / Br2; AcOH / 5 - 20 °C 2.1: NaH / dimethylsulfoxide; tetrahydrofuran / 60 °C 2.2: 90 percent / 2 h / 60 °C 3.1: 99 percent / thiophenol; AIBN / toluene / 2 h / 80 °C With 2,2'-azobis(isobutyronitrile), bromine, sodium hydride, acetic acid, thiophenol in tetrahydrofuran, dimethyl sulfoxide, toluene Bianchi, Dario A.; Cipulli, Marcos A.; Kaufman, Teodoro S.; European Journal of Organic Chemistry; nb. 24; (2003); p. 4731 - 4736 View in Reaxys Br O

Rx-ID: 13871787 View in Reaxys 120/276 Yield

Conditions & References Reaction Steps: 2 1.1: 93 percent / Br2; AcOH / 5 - 20 °C

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2.1: NaH / dimethylsulfoxide; tetrahydrofuran / 60 °C 2.2: 90 percent / 2 h / 60 °C With bromine, sodium hydride, acetic acid in tetrahydrofuran, dimethyl sulfoxide Bianchi, Dario A.; Cipulli, Marcos A.; Kaufman, Teodoro S.; European Journal of Organic Chemistry; nb. 24; (2003); p. 4731 - 4736 View in Reaxys

O O

Rx-ID: 14045698 View in Reaxys 121/276 Yield

Conditions & References Reaction Steps: 3 1: 86 percent / LiAlH4 / tetrahydrofuran / 12 h / 40 °C 2: 77 percent / NaH / tetrahydrofuran / 20 h / Heating 3: 100 percent / t-BuOK / dimethylformamide / 18 h / 20 °C With lithium aluminium tetrahydride, potassium tert-butylate, sodium hydride in tetrahydrofuran, N,N-dimethyl-formamide Van Otterlo, Willem A. L.; Pathak, Rakhi; De Koning, Charles B.; Synlett; nb. 12; (2003); p. 1859 - 1861 View in Reaxys

O OH

O Z

Rx-ID: 15107029 View in Reaxys 122/276 Yield

Conditions & References Reaction Steps: 3 1.1: dimethylformamide / 20 h / Heating 1.2: 97 percent / K2CO3 / dimethylformamide / 12 h / 80 °C 2.1: 99 percent / LiAlH4 / diethyl ether / 12 h / 20 °C 3.1: potassium t-butoxide / dimethylformamide / 0.25 h / 20 °C With lithium aluminium tetrahydride, potassium tert-butylate in diethyl ether, N,N-dimethyl-formamide De Koning, Charles B; Green, Ivan R; Michael, Joseph P; Oliveira, Jose R; Tetrahedron; vol. 57; nb. 47; (2001); p. 9623 - 9634 View in Reaxys

O O

Rx-ID: 15107030 View in Reaxys 123/276 Yield

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De Koning, Charles B; Green, Ivan R; Michael, Joseph P; Oliveira, Jose R; Tetrahedron; vol. 57; nb. 47; (2001); p. 9623 - 9634 View in Reaxys

O Z

Rx-ID: 15108756 View in Reaxys 124/276 Yield

Conditions & References Reaction Steps: 2 1: 99 percent / LiAlH4 / diethyl ether / 12 h / 20 °C 2: potassium t-butoxide / dimethylformamide / 0.25 h / 20 °C With lithium aluminium tetrahydride, potassium tert-butylate in diethyl ether, N,N-dimethyl-formamide De Koning, Charles B; Green, Ivan R; Michael, Joseph P; Oliveira, Jose R; Tetrahedron; vol. 57; nb. 47; (2001); p. 9623 - 9634 View in Reaxys

O OH

O E

Rx-ID: 15108757 View in Reaxys 125/276 Yield

4-dimethylamino-benzyl magnesium chloride

Rx-ID: 16962618 View in Reaxys 126/276 Yield

Conditions & References Reaction Steps: 2 1: 70 percent / diethyl ether / 1 h / 0 - 20 °C 2: 55 percent / p-toluenesulfonic acid hydrate / benzene / 0.5 h / Heating With toluene-4-sulfonic acid in diethyl ether, benzene Kulasegaram, Sanjitha; Kulawiec, Robert J.; Tetrahedron; vol. 54; nb. 8; (1998); p. 1361 - 1374 View in Reaxys

O O

Rx-ID: 17428449 View in Reaxys 127/276 Yield

Conditions & References Reaction Steps: 2

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1: 97.4 percent / diethyl ether / 3 h 2: 59 percent / fused potassium hydrogen sulfate, 4-t-butylcatechol / 220 °C / 20 Torr With potassium hydrogensulfate, 3,4-dihydroxy-1-tert-butylbenzene in diethyl ether Engler, Thomas A.; LaTessa, Kenneth O.; Iyengar, Rajesh; Chai, Wenying; Agrios, Konstantinos; Bioorganic and Medicinal Chemistry; vol. 4; nb. 10; (1996); p. 1755 - 1769 View in Reaxys

O O

Rx-ID: 18386615 View in Reaxys 128/276 Yield

Conditions & References Reaction Steps: 2 1: 2.) p-toluenesulfonic acid 2: 57 percent / p-dicyanobenzene / acetonitrile; H2O / 15 h / Irradiation With para-dicyanobenzene, toluene-4-sulfonic acid in water, acetonitrile Yamashita; Yamashita, Toshiaki; Yasuda; Yasuda, Masahide; Isami; Isami, Toshihiro; Tanabe; Tanabe, Kimiko; Shima; Shima, Kensuke; Tetrahedron; vol. 50; nb. 31; (1994); p. 9275 - 9286 View in Reaxys

Rx-ID: 18703507 View in Reaxys 129/276 Yield

Conditions & References Reaction Steps: 2 1: 1) t-BuOK / 1) THF, ca. 20 deg C, 2 h, 2) THF, 20 min 2: diethyl ether / 1 h / 0 °C With potassium tert-butylate in diethyl ether Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys Reaction Steps: 2 1: 1) t-BuOK / 1) THF, ca. 20 deg C, 2 h, 2) THF, 20 min 2: tetrahydrofuran / 0.25 h / -78 °C With potassium tert-butylate in tetrahydrofuran Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys Reaction Steps: 2 1: 1) t-BuOK / 1) THF, ca. 20 deg C, 2 h, 2) THF, 20 min 2: tetrahydrofuran / 1 h / -70 °C With potassium tert-butylate in tetrahydrofuran Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys

Cl O

KMnO4

Rx-ID: 22447250 View in Reaxys 130/276

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Yield

Conditions & References Reaction Steps: 3 1: HCl 2: Cl2, aq. NaOH / ethanol 3: copper chromite, quinoline / 230 - 235 °C With quinoline, hydrogenchloride, sodium hydroxide, copper (II) chromite, chlorine in ethanol Fischer,F. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 28; (1965); p. 157 - 168 View in Reaxys Reaction Steps: 3 1: (i) Zn, (ii) POCl3, (iii) aq. NaOH 2: HBr 3: aq. NaHCO3 With hydrogen bromide, sodium hydrogencarbonate Noyce,D.S.; Banitt,E.H.; Journal of Organic Chemistry; vol. 31; (1966); p. 4043 - 4047 View in Reaxys

KMnO4

Cl O

Rx-ID: 22447251 View in Reaxys 131/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: NaHSO4 / 160 °C With sodium hydrogen sulfate in diethyl ether Fischer,F. et al.; Journal fuer Praktische Chemie (Leipzig); vol. 28; (1965); p. 157 - 168 View in Reaxys Reaction Steps: 3 1: (i) Zn, (ii) POCl3, (iii) aq. NaOH 2: HBr 3: aq. NaHCO3 With hydrogen bromide, sodium hydrogencarbonate Noyce,D.S.; Banitt,E.H.; Journal of Organic Chemistry; vol. 31; (1966); p. 4043 - 4047 View in Reaxys

O O

O E

OH O

Rx-ID: 33488223 View in Reaxys 132/276 Yield

Conditions & References Reaction Steps: 7 1.1: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere 2.1: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 24 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / methanol; dichloromethane / 3 h / 20 °C / Inert atmosphere 3.2: 0 °C / pH 2 - 3 / Inert atmosphere 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere 5.1: n-butyllithium / tetrahydrofuran; toluene / 0.33 h / 0 °C / Inert atmosphere 5.2: 3.33 h / -78 - 20 °C / Inert atmosphere 6.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 6.2: 0.5 h / 20 °C / Inert atmosphere 6.3: 4.75 h / -78 - 0 °C / Inert atmosphere 7.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 20 °C / Inert atmosphere

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With dichloro bis(acetonitrile) palladium(II), lithium aluminium tetrahydride, n-butyllithium, oxalyl dichloride, di-n-butylboryl trifluoromethanesulfonate, potassium carbonate, N,N-dimethyl-formamide, sodium hydroxide in tetrahydrofuran, 1,4-dioxane, methanol, diethyl ether, dichloromethane, toluene, 1.1: Wittig reaction / 6.1: Aldol condensation / 6.2: Aldol condensation / 6.3: Aldol condensation Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L View in Reaxys

E O

Rx-ID: 33488227 View in Reaxys 133/276 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere 2: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 24 h / 20 °C / Inert atmosphere With dichloro bis(acetonitrile) palladium(II), potassium carbonate in 1,4-dioxane, dichloromethane, 1: Wittig reaction Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L View in Reaxys

Rx-ID: 33488228 View in Reaxys 134/276 Yield

Conditions & References Reaction Steps: 3 1.1: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere 2.1: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 24 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / methanol; dichloromethane / 3 h / 20 °C / Inert atmosphere 3.2: 0 °C / pH 2 - 3 / Inert atmosphere With dichloro bis(acetonitrile) palladium(II), potassium carbonate, sodium hydroxide in 1,4-dioxane, methanol, dichloromethane, 1.1: Wittig reaction Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L View in Reaxys

O O

OH O H

H O

Rx-ID: 33488229 View in Reaxys 135/276 Yield

Conditions & References Reaction Steps: 9 1.1: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere 2.1: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 24 h / 20 °C / Inert atmosphere 3.1: sodium hydroxide / methanol; dichloromethane / 3 h / 20 °C / Inert atmosphere 3.2: 0 °C / pH 2 - 3 / Inert atmosphere 4.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / Inert atmosphere

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5.1: n-butyllithium / tetrahydrofuran; toluene / 0.33 h / 0 °C / Inert atmosphere 5.2: 3.33 h / -78 - 20 °C / Inert atmosphere 6.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere 6.2: 0.5 h / 20 °C / Inert atmosphere 6.3: 4.75 h / -78 - 0 °C / Inert atmosphere 7.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 20 °C / Inert atmosphere 8.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere 9.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 20 °C / Inert atmosphere With 4-(N,N-dimethlyamino)pyridine, dichloro bis(acetonitrile) palladium(II), lithium aluminium tetrahydride, n-butyllithium, oxalyl dichloride, di-n-butylboryl trifluoromethanesulfonate, potassium carbonate, triethylamine, N,N-dimethyl-formamide, sodium hydroxide in tetrahydrofuran, 1,4-dioxane, methanol, diethyl ether, dichloromethane, toluene, 1.1: Wittig reaction / 6.1: Aldol condensation / 6.2: Aldol condensation / 6.3: Aldol condensation Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L View in Reaxys

O O

Rx-ID: 33488259 View in Reaxys 136/276 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate / acetone / 4 h / Reflux; Inert atmosphere 2: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere With potassium carbonate in 1,4-dioxane, acetone, 2: Wittig reaction Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L View in Reaxys

O O

Rx-ID: 33488260 View in Reaxys 137/276 Yield

Conditions & References Reaction Steps: 3 1: potassium carbonate / acetone / 4 h / Reflux; Inert atmosphere 2: potassium carbonate / 1,4-dioxane / 4 h / Reflux; Inert atmosphere 3: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 24 h / 20 °C / Inert atmosphere With dichloro bis(acetonitrile) palladium(II), potassium carbonate in 1,4-dioxane, dichloromethane, acetone, 2: Wittig reaction Nagaraju, Manda; Chandra, Rajesh; Gawali, Bhimrao B.; Synlett; vol. 23; nb. 10; (2012); p. 1485 - 1488; Art.No: ST-2012-D0241-L View in Reaxys

O O

N O

Rx-ID: 34132460 View in Reaxys 138/276 Yield

Conditions & References Reaction Steps: 2 1: nitric acid / dichloromethane / 2 h / 10 °C

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With nitric acid in dichloromethane, 2: |Wittig Olefination Knapkiewicz, Pawel; Skowerski, Krzysztof; Jaskolska, Dagmara E.; Barbasiewicz, Michal; Olszewski, Tomasz K.; Organic Process Research and Development; vol. 16; nb. 8; (2012); p. 1430 - 1435 View in Reaxys

Br–

P+

P O

Rx-ID: 34175275 View in Reaxys 139/276 Yield

Conditions & References Stage 1: With potassium tert-butylate in tetrahydrofuran, Time= 0.0833333h, T= 20 °C , Wittig Olefination Stage 2: in tetrahydrofuran, Wittig Olefination Baccolini, Graziano; Delpivo, Camilla; Micheletti, Gabriele; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 187; nb. 11; (2012); p. 1291 - 1302 View in Reaxys

O OH O

Rx-ID: 40666616 View in Reaxys 140/276 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate / N,N-dimethyl-formamide / 23 h / 20 °C 2: tetrahydrofuran / 0.5 h / 0 - 20 °C With potassium carbonate in tetrahydrofuran, N,N-dimethyl-formamide Grudzień, Krzysztof; Barbasiewicz, Michał; Applied Organometallic Chemistry; vol. 29; nb. 5; (2015); p. 322 - 327 View in Reaxys

O Cl

Rx-ID: 12146523 View in Reaxys 141/276 Yield

Conditions & References Reaction Steps: 2 1.1: 87 percent / anhydrous potassium carbonate / dimethylformamide / 5 h / 60 °C 2.1: sodium hydride / dimethylsulfoxide; tetrahydrofuran / 0.25 h / 20 °C 2.2: dimethylsulfoxide; tetrahydrofuran / 1 h / 60 °C With sodium hydride, potassium carbonate in tetrahydrofuran, dimethyl sulfoxide, N,N-dimethyl-formamide Giles, Robin G. F.; Green, Ivan R.; Li, Shuk-Hui; Australian Journal of Chemistry; vol. 58; nb. 8; (2005); p. 565 571 View in Reaxys

O Cl

Rx-ID: 12146524 View in Reaxys 142/276 Yield

Conditions & References Reaction Steps: 2

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1.1: 87 percent / anhydrous potassium carbonate / dimethylformamide / 5 h / 60 °C 2.1: sodium hydride / dimethylsulfoxide; tetrahydrofuran / 0.25 h / 20 °C 2.2: dimethylsulfoxide; tetrahydrofuran / 1 h / 60 °C With sodium hydride, potassium carbonate in tetrahydrofuran, dimethyl sulfoxide, N,N-dimethyl-formamide Giles, Robin G. F.; Green, Ivan R.; Li, Shuk-Hui; Australian Journal of Chemistry; vol. 58; nb. 8; (2005); p. 565 571 View in Reaxys

O Cl

Rx-ID: 12151223 View in Reaxys 143/276 Yield

Conditions & References Reaction Steps: 3 1.1: 55 percent / tert-butyl hypochlorite; acetic acid / H2O / 2 h 2.1: 87 percent / anhydrous potassium carbonate / dimethylformamide / 5 h / 60 °C 3.1: sodium hydride / dimethylsulfoxide; tetrahydrofuran / 0.25 h / 20 °C 3.2: dimethylsulfoxide; tetrahydrofuran / 1 h / 60 °C With tert-butylhypochlorite, sodium hydride, potassium carbonate, acetic acid in tetrahydrofuran, water, dimethyl sulfoxide, N,N-dimethyl-formamide Giles, Robin G. F.; Green, Ivan R.; Li, Shuk-Hui; Australian Journal of Chemistry; vol. 58; nb. 8; (2005); p. 565 571 View in Reaxys

O Cl

Rx-ID: 12151224 View in Reaxys 144/276 Yield

Rx-ID: 14430597 View in Reaxys 145/276 Yield

Conditions & References Reaction Steps: 4 1: 100 percent / aq. KOH / tetrahydrofuran / 6 h / Heating 2: 95 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 20 h / Heating 3: 63 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / -70 - 20 °C 4: 80 percent / K2CO3 / methanol / 4 h / 20 °C

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With 4-(N,N-dimethlyamino)pyridine, potassium hydroxide, n-butyllithium, potassium carbonate, triethylamine in tetrahydrofuran, methanol, hexane, dichloromethane, 3: Wittig reaction Ruffin, Brigitte; Grelier, Stephane; Nourmamode, Aziz; Castellan, Alain; Canadian Journal of Chemistry; vol. 80; nb. 9; (2002); p. 1223 - 1231 View in Reaxys

O O

Rx-ID: 14430599 View in Reaxys 146/276 Yield

Conditions & References Reaction Steps: 3 1: 100 percent / aq. KOH / tetrahydrofuran / 6 h / Heating 2: 95 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 20 h / Heating 3: 63 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / -70 - 20 °C With 4-(N,N-dimethlyamino)pyridine, potassium hydroxide, n-butyllithium, triethylamine in tetrahydrofuran, hexane, dichloromethane, 3: Wittig reaction Ruffin, Brigitte; Grelier, Stephane; Nourmamode, Aziz; Castellan, Alain; Canadian Journal of Chemistry; vol. 80; nb. 9; (2002); p. 1223 - 1231 View in Reaxys

Rx-ID: 14456672 View in Reaxys 147/276 Yield

Conditions & References Reaction Steps: 3 1: 95 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 20 h / Heating 2: 63 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / -70 - 20 °C 3: 80 percent / K2CO3 / methanol / 4 h / 20 °C With 4-(N,N-dimethlyamino)pyridine, n-butyllithium, potassium carbonate, triethylamine in tetrahydrofuran, methanol, hexane, dichloromethane, 2: Wittig reaction Ruffin, Brigitte; Grelier, Stephane; Nourmamode, Aziz; Castellan, Alain; Canadian Journal of Chemistry; vol. 80; nb. 9; (2002); p. 1223 - 1231 View in Reaxys

O O

Rx-ID: 14456673 View in Reaxys 148/276 Yield

Conditions & References Reaction Steps: 2 1: 95 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 20 h / Heating 2: 63 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / -70 - 20 °C

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With 4-(N,N-dimethlyamino)pyridine, n-butyllithium, triethylamine in tetrahydrofuran, hexane, dichloromethane, 2: Wittig reaction Ruffin, Brigitte; Grelier, Stephane; Nourmamode, Aziz; Castellan, Alain; Canadian Journal of Chemistry; vol. 80; nb. 9; (2002); p. 1223 - 1231 View in Reaxys O

O O

Rx-ID: 14457824 View in Reaxys 149/276 Yield

Conditions & References Reaction Steps: 2 1: 63 percent / n-BuLi / hexane; tetrahydrofuran / 2 h / -70 - 20 °C 2: 80 percent / K2CO3 / methanol / 4 h / 20 °C With n-butyllithium, potassium carbonate in tetrahydrofuran, methanol, hexane, 1: Wittig reaction Ruffin, Brigitte; Grelier, Stephane; Nourmamode, Aziz; Castellan, Alain; Canadian Journal of Chemistry; vol. 80; nb. 9; (2002); p. 1223 - 1231 View in Reaxys

methylacetylene metal salt

Rx-ID: 14697077 View in Reaxys 150/276 Yield

Conditions & References Reaction Steps: 2 1: 77 percent / n-BuLi; TMSCl / tetrahydrofuran 2: 72 percent / Mg; TMSCl / dimethylformamide With n-butyllithium, chloro-trimethyl-silane, magnesium in tetrahydrofuran, N,N-dimethyl-formamide Nishiguchi, Ikuzo; Matsumoto, Takeshi; Kuwahara, Takeshi; Kyoda, Makoto; Maekawa, Hirofumi; Chemistry Letters; nb. 4; (2002); p. 478 - 479 View in Reaxys

Rx-ID: 17714794 View in Reaxys 151/276 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran; diethyl ether / 2 h / Heating 2: POCl3 / pyridine / 2 h / Heating With trichlorophosphate in tetrahydrofuran, pyridine, diethyl ether Yueh, Wang; Bauld, Nathan L.; Journal of Physical Organic Chemistry; vol. 9; nb. 8; (1996); p. 529 - 538 View in Reaxys

p-tolyl-dinitromethane

Rx-ID: 17719518 View in Reaxys 152/276 Yield

Conditions & References Reaction Steps: 2 1: tetrahydrofuran; diethyl ether / 2 h / Heating

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2: POCl3 / pyridine / 2 h / Heating With trichlorophosphate in tetrahydrofuran, pyridine, diethyl ether Yueh, Wang; Bauld, Nathan L.; Journal of Physical Organic Chemistry; vol. 9; nb. 8; (1996); p. 529 - 538 View in Reaxys

linear polystyrene-supported phosphonium salt of allyl bromide

Cl O

Rx-ID: 17719683 View in Reaxys 153/276 Yield

Me4(PrO)4(μ-PrO)2W2

O O

Rx-ID: 17721836 View in Reaxys 154/276 Yield

Rx-ID: 17723093 View in Reaxys 155/276 Yield

Rx-ID: 17729129 View in Reaxys 156/276 Yield

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sodium cyanate

4.4'-dipropenyl-diphenyl

Rx-ID: 18233045 View in Reaxys 157/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-BuLi, 3.) H3O+ 2: 91 percent Spectr. / DCC / CH2Cl2 / 1 h / Ambient temperature With n-butyllithium, oxonium, dicyclohexyl-carbodiimide in dichloromethane Kawashima, Takayuki; Nakamura, Mio; Nakajo, Akira; Inamoto, Naoki; Chemistry Letters; nb. 8; (1994); p. 1483 - 1486 View in Reaxys

O O

Br O

Rx-ID: 18495150 View in Reaxys 158/276 Yield

Conditions & References Reaction Steps: 3 1: 1.) butyllithium / 1) THF, 0 deg C, 15 min; 2) THF, -78 deg C, 15 min, -78 --> room temperature, 1 h 2: bis(acetonitrile)dichloropalladium(II) / CH2Cl2 / 3 h / Ambient temperature 3: 1.) BuLi / 1) THF, -78 deg C, 30 min; 2) THF, -78 deg C, 15 min With dichloro bis(acetonitrile) palladium(II), n-butyllithium in dichloromethane Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S.; Son, Vanessa R. Lee; Yorke, Selwyn C.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1994); p. 859 864 View in Reaxys Reaction Steps: 2 1: 1.) butyllithium / 1) THF, 0 deg C, 15 min; 2) THF, -78 deg C, 15 min, -78 --> room temperature, 1 h 2: 1.) BuLi / 1) THF, -78 deg C, 30 min; 2) THF, -78 deg C, 15 min With n-butyllithium Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S.; Son, Vanessa R. Lee; Yorke, Selwyn C.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1994); p. 859 864 View in Reaxys

O HO

Br O

Rx-ID: 18495155 View in Reaxys 159/276 Yield

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View in Reaxys Reaction Steps: 2 1: 1.) butyllithium / 1) THF, 0 deg C, 15 min; 2) THF, -78 deg C, 15 min, -78 --> room temperature, 1 h 2: 1.) BuLi / 1) THF, -78 deg C, 30 min; 2) THF, -78 deg C, 15 min With n-butyllithium Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S.; Son, Vanessa R. Lee; Yorke, Selwyn C.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1994); p. 859 864 View in Reaxys

Rx-ID: 18695838 View in Reaxys 160/276 Yield

Conditions & References Reaction Steps: 2 1: 1) t-BuOK / 1a) THF, -25 deg C, 1 h, 1b) r.t., 1 h, 2) THF, -75 deg C, 15 min 2: 26 percent / tetrahydrofuran / 0.08 h / -75 °C With potassium tert-butylate in tetrahydrofuran Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys Reaction Steps: 2 1: 1) t-BuOK / 1a) THF, -25 deg C, 1 h, 1b) r.t., 1 h, 2) THF, -75 deg C, 15 min 2: 65 percent / tetrahydrofuran / 1 h / -75 °C With potassium tert-butylate in tetrahydrofuran Kauffmann, Thomas; Saelker, Reiner; Voss, Karl-Uwe; Chemische Berichte; vol. 126; nb. 6; (1993); p. 1447 1452 View in Reaxys

O O

3.4.5-trimethoxy-benzoic acid-<3.4.5-trimethoxy-benzoylidenehydrazide>

O O

Rx-ID: 18739166 View in Reaxys 161/276 Yield

Conditions & References Reaction Steps: 3 1: 1.91 g / diethyl ether / 5 h / 0 - 20 °C 2: 1.1 g / pyridine / Ambient temperature 3: 95 percent / dimethylsulfoxide / 6 h / 190 °C With pyridine in diethyl ether, dimethyl sulfoxide Kuo; Lin; Chemical and Pharmaceutical Bulletin; vol. 41; nb. 9; (1993); p. 1507 - 1512 View in Reaxys

2-oxy-phenylacetate sodium Rx-ID: 20083370 View in Reaxys 162/276

Yield

Conditions & References Reaction Steps: 4 1: 1.) Mg / 1.) ether, 2 h, 2.) ether, reflux, 1h 2: 77.7 percent / chromium trioxide, concentrated H2SO4 / H2O; acetone / 3 h / 0 - 20 °C

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3: 85 percent / 8 h / 180 - 190 °C 4: 51 percent / PPE / CHCl3; diethyl ether / 8 h / 80 °C With chromium(VI) oxide, sulfuric acid, magnesium in diethyl ether, chloroform, water, acetone Alesso, Elba N.; Tombari, Dora G.; Iglesias, Graciela Y. Moltrasio; Aguirre, Jose M.; Canadian Journal of Chemistry; vol. 65; (1987); p. 2568 - 2574 View in Reaxys

Rx-ID: 21873483 View in Reaxys 163/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) butyllithium / 1.) ether, 2.) from -78 deg C to RT 2: 80 percent / bis(acetonitrile)dichloropalladium(II) / CH2Cl2 / 3 h / Heating With dichloro bis(acetonitrile) palladium(II), n-butyllithium in dichloromethane Giles, Robin G. F.; Son, Vanessa R. Lee; Sargent, Melvyn V.; Australian Journal of Chemistry; vol. 43; nb. 4; (1990); p. 777 - 781 View in Reaxys

Rx-ID: 22793867 View in Reaxys 164/276 Yield

Conditions & References Reaction Steps: 2 2: (isomerization) / decane / 360 - 380 °C With (isomerization) in decane Wehrli; Heimgartner; Schmid; Hansen; Helvetica Chimica Acta; vol. 60; nb. 6; (1977); p. 2034 - 2061 View in Reaxys

O Br

Rx-ID: 30722386 View in Reaxys 165/276 Yield

Conditions & References Reaction Steps: 2 1.1: n-butyllithium / tetrahydrofuran / -78 - 0 °C / Inert atmosphere 1.2: -78 - 25 °C / Inert atmosphere 2.1: dichloro bis(acetonitrile) palladium(II) / dichloromethane / 25 °C With dichloro bis(acetonitrile) palladium(II), n-butyllithium in tetrahydrofuran, dichloromethane, 1.1: Wittig condensation / 1.2: Wittig condensation Mei, Mawonga N.; Hugo, Victor I.; Green, Ivan R.; Synthetic Communications; vol. 41; nb. 9; (2011); p. 1348 1356 View in Reaxys

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O O O

Rx-ID: 31046157 View in Reaxys 166/276 Yield

Conditions & References Reaction Steps: 9 1.1: potassium carbonate / benzene / Reflux 2.1: lithium aluminium tetrahydride; aluminum (III) chloride / tetrahydrofuran 3.1: ; methanesulfonamide; water; tert-butyl alcohol / 0 °C 4.1: pyridine / dichloromethane / 20 °C 5.1: potassium carbonate / methanol / 20 °C 6.1: pyridinium p-toluenesulfonate / dichloromethane 6.2: 20 °C 7.1: palladium 10 on activated carbon; hydrogen / 20 °C 8.1: potassium carbonate / acetone 9.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / Reflux With pyridine, aluminum (III) chloride, lithium aluminium tetrahydride, methanesulfonamide, palladium 10 on activated carbon, water, hydrogen, pyridinium p-toluenesulfonate, potassium carbonate, triphenylphosphine, tert-butyl alcohol, diethylazodicarboxylate in tetrahydrofuran, methanol, dichloromethane, acetone, benzene, 1.1: Wittig reaction / 3.1: Sharpless dihydroxylation / 9.1: Mitsunobu reaction Xia, Yamu; Chang, Liang; Ding, Yining; Jiao, Bin; Mendeleev Communications; vol. 20; nb. 3; (2010); p. 151 152 View in Reaxys OH

OH O

Rx-ID: 34640941 View in Reaxys 167/276 Yield

Conditions & References Reaction Steps: 2 2.1: palladium dichloride; copper dichloride; tert.-butylhydroperoxide / tetrahydrofuran; methanol / 10 h / 20 °C 2.2: 5 h / 20 °C With tert.-butylhydroperoxide, copper dichloride, palladium dichloride in tetrahydrofuran, methanol Chang, Meng-Yang; Chan, Chieh-Kai; Lin, Shin-Ying; Tetrahedron; vol. 69; nb. 5; (2013); p. 1532 - 1538 View in Reaxys

O O

Rx-ID: 36381175 View in Reaxys 168/276 Yield

Conditions & References Reaction Steps: 2 1.1: tetrahydrofuran / 1 h / 0 °C / |Inert atmosphere 1.2: 15 h / 0 - 20 °C / |Inert atmosphere 2.1: samarium diiodide; tert-butyl alcohol / tetrahydrofuran / 1 h / -78 - 20 °C / |Inert atmosphere With samarium diiodide, tert-butyl alcohol in tetrahydrofuran

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Schaefer, Sara L.; Roberts, Connor L.; Volz, Erasmus O.; Grasso, Monika R.; O'Neil, Gregory W.; Tetrahedron Letters; vol. 54; nb. 45; (2013); p. 6125 - 6128 View in Reaxys

Rx-ID: 41660273 View in Reaxys 169/276 Yield

Conditions & References Reaction Steps: 5 1: diethyl ether; tetrahydrofuran / 2.25 h / 20 °C / |Inert atmosphere; |Cooling with ice 2: DBU / benzene / 2 h / 20 °C 3: triethylamine / diethyl ether / 2 h / 20 °C / |Inert atmosphere; |Cooling with ice 4: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 2.5 h / 20 °C 5: DBU / DMFA / 2 h / 80 °C With DBU, triethylamine tris(hydrogen fluoride), triethylamine in tetrahydrofuran, diethyl ether, DMFA, benzene Immoos, John E.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 58; nb. 11-12; (2015); p. 419 424 View in Reaxys

O O

EtMgHal O

Rx-ID: 7431222 View in Reaxys 170/276 Yield

Conditions & References With acetic anhydride, 1) Et2O, reflux, 30 min, 2) reflux, 5 h, Yield given. Multistep reaction Schmidt, Arthur H.; Kircher, Gunnar; Spring, Mathias; Hendriok, Markus W.; Kuenz, Christian; Advanced Synthesis and Catalysis; vol. 339; nb. 6; (1997); p. 564 - 574 View in Reaxys

EtMgHal

Rx-ID: 8067129 View in Reaxys 171/276 Yield

Conditions & References With toluene-4-sulfonic acid, 1) Et2O, reflux, 30 min, 2) toluene, reflux, 1 h, Yield given. Multistep reaction Schmidt, Arthur H.; Kircher, Gunnar; Spring, Mathias; Hendriok, Markus W.; Kuenz, Christian; Advanced Synthesis and Catalysis; vol. 339; nb. 6; (1997); p. 564 - 574 View in Reaxys

O O

O Z

Rx-ID: 12018511 View in Reaxys 172/276 Yield

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With lithium aluminium tetrahydride, potassium tert-butylate, sodium hydride in tetrahydrofuran, N,N-dimethyl-formamide Pathak, Rakhi; Panayides, Jenny-Lee; Jeftic, Tanya D.; De Koning, Charles B.; Van Otterlo, Willem A.L.; South African Journal of Chemistry; vol. 60; (2007); p. 1 - 7 View in Reaxys

O O

Rx-ID: 12018512 View in Reaxys 173/276 Yield

Conditions & References Reaction Steps: 3 1: 86 percent / LiAlH4 / tetrahydrofuran / 12 h / 40 °C 2: 77 percent / NaH / tetrahydrofuran / 20 h / Heating 3: KO-tert-Bu / dimethylformamide / 16 h / 20 °C With lithium aluminium tetrahydride, potassium tert-butylate, sodium hydride in tetrahydrofuran, N,N-dimethyl-formamide Pathak, Rakhi; Panayides, Jenny-Lee; Jeftic, Tanya D.; De Koning, Charles B.; Van Otterlo, Willem A.L.; South African Journal of Chemistry; vol. 60; (2007); p. 1 - 7 View in Reaxys

Rx-ID: 13990604 View in Reaxys 174/276 Yield

Conditions & References Reaction Steps: 2 1: BF3*Et2O / hexane / 20 °C 2: KI; CuI / hexamethylphosphoric acid triamide With copper(l) iodide, boron trifluoride diethyl etherate, potassium iodide in N,N,N',N',N'',N''-hexamethylphosphoric triamide, hexane, 1: aldol Grob reaction Bidet; McGuigan; Andrei; Snoeck; De Clercq; Balzarini; Nucleosides, Nucleotides and Nucleic Acids; vol. 22; nb. 5-8; (2003); p. 817 - 819 View in Reaxys

O N O

N N

Rx-ID: 15507653 View in Reaxys 175/276 Yield

Conditions & References Reaction Steps: 2 1: 95 percent / ethanol / 2 h / 20 °C 2: 85 percent / aq. H2SO4 / 1.5 h / -20 °C With sulfuric acid in ethanol Trofimova; Fedotov; Mochalov; Shabarov; Zefirov; Chemistry of Heterocyclic Compounds; vol. 36; nb. 10; (2000); p. 1198 - 1205 View in Reaxys

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Rx-ID: 17630774 View in Reaxys 176/276 Yield

Conditions & References Reaction Steps: 2 2: 5.5 percent / m-chloroperbenzoic acid / CHCl3 / 24 h / 0 °C With 3-chloro-benzenecarboperoxoic acid in chloroform Giles, Robin G. F.; Rickards, Rodney W.; Senanayake, Badra S.; Journal of the Chemical Society - Perkin Transactions 1; nb. 18; (1996); p. 2241 - 2248 View in Reaxys

Rx-ID: 18494803 View in Reaxys 177/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) BuLi / 1) THF, 0 deg C, 5 min; 2) THF, -78 deg C, 15 min, room temperature, 1.5 h 2: 85 percent / bis(acetonitrile)dichloropalladium(II) / CH2Cl2 / 2 h / Ambient temperature With dichloro bis(acetonitrile) palladium(II), n-butyllithium in dichloromethane Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S.; Son, Vanessa R. Lee; Yorke, Selwyn C.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1994); p. 865 874 View in Reaxys

Br O

Rx-ID: 18495154 View in Reaxys 178/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) butyllithium / 1) THF, 0 deg C, 15 min; 2) THF, -78 deg C, 15 min, -78 --> room temperature, 1 h 2: bis(acetonitrile)dichloropalladium(II) / CH2Cl2 / 3 h / Ambient temperature With dichloro bis(acetonitrile) palladium(II), n-butyllithium in dichloromethane Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S.; Son, Vanessa R. Lee; Yorke, Selwyn C.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1994); p. 859 864 View in Reaxys

O Br

Rx-ID: 18495191 View in Reaxys 179/276 Yield

Conditions & References Reaction Steps: 2

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1: 1.) BuLi / 1) THF, 0 deg C; 2) THF, -78 deg C --> room temperature, 1 h 2: 82 percent / NaH / dimethylformamide / 0.33 h / 55 °C With n-butyllithium, sodium hydride in N,N-dimethyl-formamide Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S.; Son, Vanessa R. Lee; Yorke, Selwyn C.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1994); p. 865 874 View in Reaxys

Rx-ID: 18495192 View in Reaxys 180/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) BuLi / 1) THF, 0 deg C; 2) THF, -78 deg C --> room temperature, 1 h 2: NaH / dimethylformamide / 0.33 h / 55 °C With n-butyllithium, sodium hydride in N,N-dimethyl-formamide Giles, Robin G. F.; Green, Ivan R.; Knight, Lorraine S.; Son, Vanessa R. Lee; Yorke, Selwyn C.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 7; (1994); p. 865 874 View in Reaxys HO

HO O

Rx-ID: 19186181 View in Reaxys 181/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / 3 h / Heating 2: glacial acetic acid / 3 h / Heating With acetic acid in diethyl ether Arnarp; Bielawski; Dahlin; Dahlman; Enzell; Pettersson; Acta chemica Scandinavica (Copenhagen, Denmark : 1989); vol. 43; nb. 1; (1989); p. 44 - 50 View in Reaxys HO

HO O

Rx-ID: 19186182 View in Reaxys 182/276 Yield

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NH 2

O O O

Rx-ID: 19408774 View in Reaxys 183/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-BuLi / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, overnight 2: aq. Na2S2O4 / methanol / 0.5 h / Ambient temperature With n-butyllithium, sodium dithionite in methanol Hibino, Satoshi; Sugino, Eiichi; Heterocycles; vol. 26; nb. 7; (1987); p. 1883 - 1889 View in Reaxys

O O O

H N

Rx-ID: 19408775 View in Reaxys 184/276 Yield

Conditions & References Reaction Steps: 3 1: 1.) n-BuLi / 1.) THF, hexane, 30 min, 2.) THF, hexane, RT, overnight 2: aq. Na2S2O4 / methanol / 0.5 h / Ambient temperature 3: K2CO3 / CHCl3 / 2 h / Ambient temperature With n-butyllithium, sodium dithionite, potassium carbonate in methanol, chloroform Hibino, Satoshi; Sugino, Eiichi; Heterocycles; vol. 26; nb. 7; (1987); p. 1883 - 1889 View in Reaxys

Rx-ID: 20000199 View in Reaxys 185/276 Yield

Conditions & References Reaction Steps: 3 1: 98 percent / Mg / diethyl ether / 1 h / Heating 2: 83 percent / PCl5 / 0.5 h 3: KOtBu / dimethylsulfoxide / 0.25 h / Ambient temperature With phosphorus pentachloride, potassium tert-butylate, magnesium in diethyl ether, dimethyl sulfoxide Hoehn, Juergen; Weyerstahl, Peter; Chemische Berichte; vol. 116; nb. 2; (1983); p. 808 - 814 View in Reaxys

Rx-ID: 20581698 View in Reaxys 186/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / 2 h 2: AcOH, conc. H2SO4 / 0.5 h / Heating With sulfuric acid, acetic acid in diethyl ether

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Atmaram, Shiravante; Forrester, Alexander R.; Gill, Melvin; Thomson, Ronald H.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1981); p. 1721 - 1724 View in Reaxys

Rx-ID: 22383425 View in Reaxys 187/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether 2: TsOH / toluene / Heating With toluene-4-sulfonic acid in diethyl ether, toluene Ruwet,A.; Renson,M.; Bulletin des Societes Chimiques Belges; vol. 79; (1970); p. 593 - 599 View in Reaxys

Rx-ID: 22385041 View in Reaxys 188/276 Yield

Rx-ID: 22417868 View in Reaxys 189/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / Heating 2: DMSO / 165 °C With dimethyl sulfoxide in diethyl ether Cabiddu,S. et al.; Gazzetta Chimica Italiana; vol. 98; (1968); p. 800 - 809 View in Reaxys N

O HO

Rx-ID: 36739125 View in Reaxys 190/276 Yield

Conditions & References Reaction Steps: 4 1.1: sodium acetate; formic acid; hydroxylamine hydrochloride / 2 h / |Reflux 1.2: 4 h / |Reflux 2.1: aluminum (III) chloride; sodium iodide / acetonitrile / 5 h / 70 °C

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3.1: sulfuric acid / 20 °C 4.1: water; bis-triphenylphosphine-palladium(II) chloride; sodium carbonate / acetonitrile; ethanol / 0.33 h / 120 °C / | Microwave irradiation With aluminum (III) chloride, bis-triphenylphosphine-palladium(II) chloride, formic acid, sulfuric acid, hydroxylamine hydrochloride, water, sodium acetate, sodium carbonate, sodium iodide in ethanol, acetonitrile Patent; ORION CORPORATION; AHLMARK, Marko; DIN BELLE, David; KAUPPALA, Mika; LUIRO, Anne; PAJUNEN, Taina; PYSTYNEN, Jarmo; TIAINEN, Eija; VAISMAA, Matti; MESSINGER, Josef; WO2013/175053; (2013); (A1) English View in Reaxys

Rx-ID: 41660274 View in Reaxys 191/276 Yield

Conditions & References Reaction Steps: 4 1: diethyl ether; tetrahydrofuran / 2.25 h / 20 °C / |Inert atmosphere; |Cooling with ice 2: triethylamine / diethyl ether / 2.5 h / |Inert atmosphere; |Cooling with ice 3: triethylamine / benzene / 3.5 h / 20 °C / |Cooling with ice 4: DBU / DMFA / 12 h / 80 °C With DBU, triethylamine in tetrahydrofuran, diethyl ether, DMFA, benzene Immoos, John E.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 58; nb. 11-12; (2015); p. 419 424 View in Reaxys F F

F F

Rx-ID: 41900062 View in Reaxys 192/276 Yield

Conditions & References Reaction Steps: 3 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / -30 °C / |Inert atmosphere 1.2: 3 h / |Inert atmosphere 2.1: sec.-butyllithium / tetrahydrofuran; cyclohexane; hexane / 2 h / -70 °C / |Inert atmosphere 2.2: 12 h / |Inert atmosphere 2.3: 3 h / -30 °C / |Inert atmosphere 3.1: potassium carbonate; tetrabutylammomium bromide; tetrakis(triphenylphosphine) palladium(0); Solmix A-11 / water; toluene / 3 h / |Inert atmosphere; |Reflux With tetrakis(triphenylphosphine) palladium(0), Solmix A-11, potassium tert-butylate, tetrabutylammomium bromide, sec.-butyllithium, potassium carbonate in tetrahydrofuran, hexane, cyclohexane, water, toluene Patent; JNC Corporation; JNC Petrochemical Corporation; TANAKA, Hiroyuki; ENDOU, Hiroshi; (91 pag.); EP2960226; (2015); (A1) English View in Reaxys

OH B

Rx-ID: 43264510 View in Reaxys 193/276 Yield

Conditions & References Reaction Steps: 3 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / -40 - -30 °C / |Inert atmosphere 1.2: 0.5 h / -40 - -30 °C / |Inert atmosphere

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2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -60 °C / |Inert atmosphere 2.2: 7 h / -70 - 20 °C / |Inert atmosphere 3.1: hydrogenchloride / water / 0.5 h / |Inert atmosphere With hydrogenchloride, n-butyllithium, potassium tert-butylate in tetrahydrofuran, hexane, water Patent; JNC CORPORATION; JNC PETROCHEMICAL CORPORATION; GOTO, MAYUMI; TANAKA, HIROYUKI; (104 pag.); JP2016/37458; (2016); (A) Japanese View in Reaxys

O B

Rx-ID: 43264513 View in Reaxys 194/276 Yield

Conditions & References Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 2 h / -40 - -30 °C / |Inert atmosphere 1.2: 0.5 h / -40 - -30 °C / |Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -60 °C / |Inert atmosphere 2.2: 7 h / -70 - 20 °C / |Inert atmosphere With n-butyllithium, potassium tert-butylate in tetrahydrofuran, hexane Patent; JNC CORPORATION; JNC PETROCHEMICAL CORPORATION; GOTO, MAYUMI; TANAKA, HIROYUKI; (104 pag.); JP2016/37458; (2016); (A) Japanese View in Reaxys O

O O O

Rx-ID: 44038148 View in Reaxys 195/276 Yield

Conditions & References Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 6 h / 20 °C 1.2: 12 h / |Reflux 2.1: potassium hydoxide / methanol; water / 4 h / |Reflux With potassium tert-butylate, potassium hydoxide in tetrahydrofuran, methanol, water Patent; Tokyo University of Science; Arimitsu, Yuko; (61 pag.); JP5765851; (2015); (B2) Japanese View in Reaxys

O HO

Rx-ID: 44038166 View in Reaxys 196/276 Yield

Conditions & References Reaction Steps: 3 1.1: potassium carbonate / acetone / 5 h / |Reflux 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C 2.2: 6 h / 20 °C 3.1: potassium hydoxide / methanol; water / 6 h / |Reflux With potassium tert-butylate, potassium carbonate, potassium hydoxide in tetrahydrofuran, methanol, water, acetone Patent; Tokyo University of Science; Arimitsu, Yuko; (61 pag.); JP5765851; (2015); (B2) Japanese View in Reaxys

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O O

O HO

Rx-ID: 44038172 View in Reaxys 197/276 Yield

Conditions & References Reaction Steps: 2 1.1: potassium carbonate / acetone / 5 h / |Reflux 2.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C 2.2: 6 h / 20 °C With potassium tert-butylate, potassium carbonate in tetrahydrofuran, acetone Patent; Tokyo University of Science; Arimitsu, Yuko; (61 pag.); JP5765851; (2015); (B2) Japanese View in Reaxys O

Rx-ID: 44038177 View in Reaxys 198/276 Yield

Conditions & References Reaction Steps: 2 1.1: potassium tert-butylate / tetrahydrofuran / 1 h / 20 °C 1.2: 6 h / 20 °C 2.1: potassium hydoxide / methanol; water / 6 h / |Reflux With potassium tert-butylate, potassium hydoxide in tetrahydrofuran, methanol, water Patent; Tokyo University of Science; Arimitsu, Yuko; (61 pag.); JP5765851; (2015); (B2) Japanese View in Reaxys

Rx-ID: 44861182 View in Reaxys 199/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether / 2 h / 0 - 20 °C / Inert atmosphere 2: toluene-4-sulfonic acid / toluene / 2 h / 100 °C With toluene-4-sulfonic acid in diethyl ether, toluene Patent; FORUM PHARMACEUTICALS INC.; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; HARRISON, Bryce, Alden; (273 pag.); WO2017/31325; (2017); (A1) English View in Reaxys

Rx-ID: 164205 View in Reaxys 200/276 Yield

Conditions & References Erhitzen des nach der Hydrolyse erhaltenen Reaktionsprodukts mit KHSO4 auf 160grad Marvel; Botteron; Journal of the American Chemical Society; vol. 63; (1941); p. 1482 View in Reaxys

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O O

Rx-ID: 308111 View in Reaxys 201/276 Yield

Conditions & References With propionic acid sodium salt, propionic acid anhydride, T= 200 °C Lora Tamayo; Viguera; Martin Panizo; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 41; (1945); p. 1325,1331 View in Reaxys

O O

O E

Rx-ID: 659694 View in Reaxys 202/276 Yield

Conditions & References With sodium propargylate, T= 180 °C Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 814 View in Reaxys O H N

NH 2 Z

Rx-ID: 21282086 View in Reaxys 203/276 Yield

Conditions & References Reaction Steps: 2 2: benzene / 0.75 h / Irradiation in benzene Padwa, Albert; Nahm, Steven; Journal of Organic Chemistry; vol. 46; nb. 7; (1981); p. 1402 - 1409 View in Reaxys

Rx-ID: 22146893 View in Reaxys 204/276 Yield

Conditions & References Reaction Steps: 2 1: methanol.KOH 2: diethyl ether / Hydrolysis.Erhitzen des erhaltenen Reaktionsprodukts unter vermindertem Druck With potassium hydroxide, diethyl ether Lora Tamayo; Martin Panizo; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 40; (1944); p. 394,399 View in Reaxys

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Reaction Steps: 2 1: alkaline solution 2: zerlegen des Produktes mit verd. Schwefelsaeure und Destillation With alkaline solution Hell; Hofmann; Chemische Berichte; vol. 38; (1905); p. 1676 View in Reaxys Reaction Steps: 3 1: alkaline solution 3: diluted sulfuric acid / durch Destillation With alkaline solution, sulfuric acid Hell; Hofmann; Chemische Berichte; vol. 38; (1905); p. 1676 View in Reaxys Reaction Steps: 2 1: alkaline solution 2: zerlegen des Produktes mit verd. Schwefelsaeure und Destillation With alkaline solution Hell; Hofmann; Chemische Berichte; vol. 38; (1905); p. 1676 View in Reaxys

H Sb

O P

Sb P O

Rx-ID: 44814785 View in Reaxys 205/276 Yield

Conditions & References in tetrahydrofuran, Time= 2.5h, T= -90 - 20 °C , Wittig Olefination, Overall yield = 87 percent Uchiyama, Yosuke; Ohtsuki, Takemaru; Murakami, Rikiya; Shibata, Munenori; Sugimoto, Jun; European Journal of Organic Chemistry; vol. 2017; nb. 1; (2017); p. 159 - 174 View in Reaxys

Rx-ID: 725737 View in Reaxys 206/276 Yield

Conditions & References zerlegen des Produktes mit verd. Schwefelsaeure und Destillation Hell; Bauer; Chemische Berichte; vol. 36; (1903); p. 1188 View in Reaxys Hell; Hofmann; Chemische Berichte; vol. 38; (1905); p. 1676 View in Reaxys With diethyl ether, Hydrolysis.Erhitzen des erhaltenen Reaktionsprodukts unter vermindertem Druck Lora Tamayo; Martin Panizo; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 40; (1944); p. 394,399 View in Reaxys Escoruela; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 42; (1946); p. 219,228 View in Reaxys

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Rx-ID: 1176968 View in Reaxys 207/276 Yield

Conditions & References (i), (ii) (dehydration), Multistep reaction Schmid,G.H.; Nowlan,V.J.; Canadian Journal of Chemistry; vol. 54; (1976); p. 695 - 702 View in Reaxys With P2O5, 1.) diethyl ether, 2.) benzene, reflux, Multistep reaction Glatzhofer, Daniel T.; Longone, Daniel T.; Tetrahedron Letters; vol. 27; nb. 49; (1986); p. 5923 - 5926 View in Reaxys

O O

Rx-ID: 22651052 View in Reaxys 208/276 Yield

Conditions & References Reaction Steps: 2 1: (i) NaH, DMSO, (ii) /BRN= 2110812/ 2: diethyl ether in diethyl ether Taub,D. et al.; Tetrahedron; vol. 24; (1968); p. 2443 - 2461 View in Reaxys Reaction Steps: 2 1: tetrahydrofuran 2: (i) NaH, DMSO, (ii) /BRN= 2972629/ in tetrahydrofuran Taub,D. et al.; Tetrahedron; vol. 24; (1968); p. 2443 - 2461 View in Reaxys

F F

Rx-ID: 19606276 View in Reaxys 209/276 Yield

Conditions & References Reaction Steps: 2 1: 1.) n-BuLi / 1.) ether, -78 deg C 2: 1.) n-BuLi / 1.) THF, -78 deg C With n-butyllithium Turner, William R.; Suto, Mark J.; Tetrahedron Letters; vol. 34; nb. 2; (1993); p. 281 - 284 View in Reaxys

O O

O OH

Rx-ID: 22651051 View in Reaxys 210/276 Yield

Conditions & References Reaction Steps: 2

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1: (i) NaH, DMSO, (ii) /BRN= 2110812/ 2: KOH / 180 - 185 °C With potassium hydroxide Taub,D. et al.; Tetrahedron; vol. 24; (1968); p. 2443 - 2461 View in Reaxys

O N

N O

Rx-ID: 34132461 View in Reaxys 211/276 Yield

Conditions & References Reaction Steps: 2 1: potassium carbonate; caesium carbonate With potassium carbonate, caesium carbonate, 2: |Wittig Olefination Knapkiewicz, Pawel; Skowerski, Krzysztof; Jaskolska, Dagmara E.; Barbasiewicz, Michal; Olszewski, Tomasz K.; Organic Process Research and Development; vol. 16; nb. 8; (2012); p. 1430 - 1435 View in Reaxys

Rx-ID: 605650 View in Reaxys 212/276 Yield

Conditions & References With benzene Lora Tamayo; Martin Panizo; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 41; (1945); p. 1151,1160 View in Reaxys (i), (ii) aq. H2SO4, Multistep reaction Hamacher; Archiv der Pharmazie; vol. 307; nb. 4; (1974); p. 309 - 315 View in Reaxys

E 2H

Rx-ID: 22793870 View in Reaxys 213/276 Yield

Conditions & References Reaction Steps: 2 2: decane / 370 °C in decane Wehrli; Heimgartner; Schmid; Hansen; Helvetica Chimica Acta; vol. 60; nb. 6; (1977); p. 2034 - 2061 View in Reaxys

Rx-ID: 479665 View in Reaxys 214/276

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Yield

Conditions & References With diethyl ether, ethylmagnesium bromide, benzene, Erwaermen des Reaktionsprodukts in Aethanol mit wss. HCl Badger; Journal of the Chemical Society; (1952); p. 1175,1177 View in Reaxys

O O

Rx-ID: 607693 View in Reaxys 215/276 Yield

Conditions & References With sodium proprionate Moureu; Annales de Chimie (Cachan, France); vol. <7> 15; (1898); p. 135 View in Reaxys Moureu; Chauvet; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 412 View in Reaxys

Br– P+

Rx-ID: 2392100 View in Reaxys 216/276 Yield

Conditions & References With potassium carbonate in methanol, Time= 1h, T= 65 °C , Yield given Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Tetrahedron; vol. 42; nb. 14; (1986); p. 3813 - 3824 View in Reaxys With potassium carbonate in methanol, Time= 1h, T= 65 °C , other arylaldehyde: anisaldehyde, Product distribution, Quantum yield Le Bigot, Y.; El Gharbi, R.; Delmas, M.; Gaset, A.; Tetrahedron; vol. 42; nb. 14; (1986); p. 3813 - 3824 View in Reaxys O O

Rx-ID: 4310854 View in Reaxys 217/276 Yield

Conditions & References in diethyl ether Mueller,A.; Lempert-Sreter,M.; Monatshefte fuer Chemie; vol. 96; (1965); p. 369 - 380 View in Reaxys

Br–

H P+

Rx-ID: 4829577 View in Reaxys 218/276 Yield

Conditions & References With potassium hexamethylsilazane, 1.) THF, 0 deg C, 2 h, 2.) THF, -78 deg C, 2 h; -78 deg C to r.t., 4 h, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Lawrence, Nicholas J.; Beynek, Hayrettin; Synlett; nb. 5; (1998); p. 497 - 498

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View in Reaxys O O O

EtMgHal

Rx-ID: 7548279 View in Reaxys 219/276 Yield

Conditions & References 1) Et2O, reflux, 30 min, 2) 170 deg C, 2 h, Yield given. Multistep reaction Schmidt, Arthur H.; Kircher, Gunnar; Spring, Mathias; Hendriok, Markus W.; Kuenz, Christian; Advanced Synthesis and Catalysis; vol. 339; nb. 6; (1997); p. 564 - 574 View in Reaxys

EtMgHal

Rx-ID: 7599738 View in Reaxys 220/276 Yield

EtMgHal

Rx-ID: 7648626 View in Reaxys 221/276 Yield

EtMgHal E

Rx-ID: 8116793 View in Reaxys 222/276 Yield

concentrated NaOH-solution O

Rx-ID: 19972278 View in Reaxys 223/276 Yield

Conditions & References Reaction Steps: 2 1: H2O

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2: 85percent H3PO4 / Heating With phosphoric acid, water Gleiter, Rolf; Hopf, Henning; Eckert-Maksic, Mirjana; Noble, Karl-Ludwig; Chemische Berichte; vol. 113; nb. 10; (1980); p. 3401 - 3403 View in Reaxys

HO E

O O

Rx-ID: 22073663 View in Reaxys 224/276 Yield

Conditions & References Reaction Steps: 3 1: sodium propionate / Erwaermen des Reaktionsprodukts mit aethanol. KOH 2: Na2S2O8; aqueous NaOH 3: K2CO3; acetone With sodium hydroxide, sodium peroxodisulphate, propionic acid sodium salt, potassium carbonate, acetone Seshadri; Thiruvengadam; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 32; (1950); p. 110,112 View in Reaxys HO

O O

Rx-ID: 22073668 View in Reaxys 225/276 Yield

Conditions & References Reaction Steps: 2 1: sodium propionate / Erwaermen des Reaktionsprodukts mit aethanol. KOH 2: Na2S2O8; aqueous NaOH With sodium hydroxide, sodium persulfate, sodium proprionate Seshadri; Thiruvengadam; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 32; (1950); p. 110,112 View in Reaxys

I O

Rx-ID: 22110858 View in Reaxys 226/276 Yield

Conditions & References Reaction Steps: 2 1: benzene; ethyl magnesium bromide; diethyl ether 2: P2O5; diethyl ether With diethyl ether, ethylmagnesium bromide, phosphorus pentoxide, benzene Frejka; Zamis; ; vol. 63; (1950); p. 157; ; (1953); p. 2131 View in Reaxys O O O

Rx-ID: 22126886 View in Reaxys 227/276 Yield

Conditions & References Reaction Steps: 2 2: HCl / Erhitzen des Chlorids mit Pyridin auf 120grad

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With hydrogenchloride Klages; Chemische Berichte; vol. 37; (1904); p. 3995 View in Reaxys

O O O OH

Rx-ID: 22129296 View in Reaxys 228/276 Yield

Conditions & References Reaction Steps: 2 1: 210 °C 2: KOH; water / 170 °C With potassium hydroxide, water Claisen; Eisleb; Justus Liebigs Annalen der Chemie; vol. 401; (1913); p. 44 View in Reaxys

Rx-ID: 22145649 View in Reaxys 229/276 Yield

O Z

OH O

O O

Rx-ID: 22146785 View in Reaxys 230/276 Yield

Conditions & References Reaction Steps: 2 1: benzene 2: toluene / 170 - 180 °C With toluene, benzene Lora Tamayo; Martin Panizo; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 41; (1945); p. 1151,1160 View in Reaxys

O OH

Rx-ID: 22147169 View in Reaxys 231/276 Yield

Conditions & References Reaction Steps: 3 1: potassium carbonate; alcohol

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2: 210 °C 3: KOH; water / 170 °C With potassium hydroxide, ethanol, water, potassium carbonate Claisen; Eisleb; Justus Liebigs Annalen der Chemie; vol. 401; (1913); p. 44 View in Reaxys H O

Rx-ID: 22200243 View in Reaxys 232/276 Yield

Conditions & References Reaction Steps: 2 1: diethyl ether With diethyl ether Klages; Chemische Berichte; vol. 36; (1903); p. 621 View in Reaxys

Rx-ID: 22203260 View in Reaxys 233/276 Yield

Conditions & References Reaction Steps: 2 2: diluted sulfuric acid / durch Destillation With sulfuric acid Hell; Hofmann; Chemische Berichte; vol. 38; (1905); p. 1676 View in Reaxys

HO O

O O

Rx-ID: 22237234 View in Reaxys 234/276 Yield

Conditions & References Reaction Steps: 3 1: aq.-ethanolic HCl; toluene; amalgamated zinc 2: K2CO3; acetone 3: KOH; ethanol With hydrogenchloride, potassium hydroxide, amalgamated zinc, ethanol, potassium carbonate, acetone, toluene Clemo; Duxbury; Journal of the Chemical Society; (1952); p. 3844,3846 View in Reaxys Br

Rx-ID: 22364383 View in Reaxys 235/276 Yield

Conditions & References Reaction Steps: 2 1: benzene 2: diethyl ether / Erhitzen des vom Aether befreiten Reaktionsgemisches auf 100grad With diethyl ether, benzene

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Cartwright; Haworth; Journal of the Chemical Society; (1944); p. 535 View in Reaxys

Rx-ID: 22578879 View in Reaxys 236/276 Yield

Conditions & References Reaction Steps: 2 2: KHSO4 With potassium hydrogensulfate Guyon,R.; Villa,P.; Bulletin de la Societe Chimique de France; (1975); p. 2584 - 2592 View in Reaxys

E O

Rx-ID: 58428 View in Reaxys 237/276 Yield

Conditions & References With diethyl ether, Eindampfen des Reaktionsgemisches Mauthner; Journal fuer Praktische Chemie (Leipzig); vol. <2> 107; (1924); p. 107 View in Reaxys

Mg N

Rx-ID: 462371 View in Reaxys 238/276 Yield

Conditions & References With diethyl ether, man destilliert das erhaltene, oelige Aethyl-<2.4-bis-dimethylamino-phenyl>-carbinol unter 15 mm Druck Sachs; Appenzeller; Chemische Berichte; vol. 41; (1908); p. 103 View in Reaxys

O O

Rx-ID: 579259 View in Reaxys 239/276 Yield

Conditions & References With propionic acid sodium salt Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 814 View in Reaxys

O O

Rx-ID: 606952 View in Reaxys 240/276 Yield

Conditions & References With diethyl ether, Hydrolysis.Erhitzen der erhaltenen Reaktionsprodukts unter 25 bis 29 Torr Escoruela; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 42; (1946); p. 219,228

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View in Reaxys

Rx-ID: 607535 View in Reaxys 241/276 Yield

Rx-ID: 608182 View in Reaxys 242/276 Yield

Conditions & References With diethyl ether, Behandeln des Reaktionsproduktes mit verd. Schwefelsaeure Pauly; v. Buttlar; Justus Liebigs Annalen der Chemie; vol. 383; (1911); p. 278 View in Reaxys HO

O O

Rx-ID: 659489 View in Reaxys 243/276 Yield

Conditions & References With propionic acid sodium salt, Erwaermen des Reaktionsprodukts mit aethanol. KOH Seshadri; Thiruvengadam; Proceedings - Indian Academy of Sciences, Section A; vol. <A> 32; (1950); p. 110,112 View in Reaxys

O E

O O

Rx-ID: 659673 View in Reaxys 244/276 Yield

Conditions & References With sodium propargylate Rousset; Bulletin de la Societe Chimique de France; vol. <3> 17; (1897); p. 814 View in Reaxys

O I

Rx-ID: 718623 View in Reaxys 245/276 Yield

Conditions & References With diethyl ether, Hydrolysis.Erhitzen des erhaltenen Reaktionsprodukts Hudson; Robinson; Journal of the Chemical Society; (1941); p. 715,720 View in Reaxys

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Rx-ID: 718671 View in Reaxys 246/276 Yield

Conditions & References With diethyl ether, Hydrolysis.Erhitzen des erhaltenen Reaktionsprodukts Lora Tamayo; Martin Panizo; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 40; (1944); p. 394,399 View in Reaxys

Mg O

Rx-ID: 5100637 View in Reaxys 247/276 Yield

Conditions & References in tetrahydrofuran, Time= 0.75h, Heating, Yield given Schmidt, Arthur H.; Kircher, Gunnar; Zylla, Joerg; Veit, Stephan; Journal of the Chemical Society - Perkin Transactions 1; nb. 4; (1999); p. 409 - 414 View in Reaxys

Rx-ID: 5105516 View in Reaxys 248/276 Yield

polymer-PPh2 (1+)-CH2CH3*I(1-)

O O

Rx-ID: 5958208 View in Reaxys 249/276 Yield

Conditions & References With HMDS, 1.) THF, r.t., 30 min, 2.) THF, r.t., 20 min, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Bolli, Martin H.; Ley, Steven V.; Journal of the Chemical Society - Perkin Transactions 1; nb. 15; (1998); p. 2243 2246 View in Reaxys O

O O

polymer-PPh2 (1+)-CH2CH3*I(1-)

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Rx-ID: 7162413 View in Reaxys 250/276 Yield

O Z

polymer-PPh2 (1+)-CH2CH3*I(1-) O

Rx-ID: 7244962 View in Reaxys 251/276 Yield

1.3.5-trimethyl-2.4.6-tris-<2-hydroxy-phenyl>-cyclohexane

Rx-ID: 7429757 View in Reaxys 252/276 Yield

Conditions & References With diethyl ether, Erhitzen des nach Hydrolyse erhaltenen Reaktionsprodukts auf 130grad Grumez; Annales de Chimie (Cachan, France); vol. <11> 10; (1938); p. 378,387 View in Reaxys O O

Na +

O–

Rx-ID: 718670 View in Reaxys 253/276 Yield

Conditions & References With propionic acid anhydride Moureu; Bulletin de la Societe Chimique de France; vol. <3> 15; (1896); p. 1022,1024; Annales de Chimie (Cachan, France); vol. <7> 15; (1898); p. 137 View in Reaxys O Br

H N

NH 2 E

Rx-ID: 1670106 View in Reaxys 254/276 Yield

Conditions & References Yield given. Multistep reaction

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Padwa, Albert; Nahm, Steven; Journal of Organic Chemistry; vol. 46; nb. 7; (1981); p. 1402 - 1409 View in Reaxys O

Na + O–

2-hydroxy-1.2-bis-<4-methoxy-naphthyl-(1)>-ethanone-(1) E

Rx-ID: 8119373 View in Reaxys 255/276 Yield

Conditions & References T= 200 °C Lora Tamayo; Viguera; Martin Panizo; Anales de la Real Sociedad Espanola de Fisica y Quimica; vol. 41; (1945); p. 1325,1331 View in Reaxys

Rx-ID: 725606 View in Reaxys 256/276 Yield

HO E

2-chloro-benzenediazonium-(1)-chloride O

Rx-ID: 18106560 View in Reaxys 257/276 Yield

Conditions & References Reaction Steps: 2 Yasuda, Masahide; Sone, Tatsuya; Tanabe, Kimiko; Shima, Kensuke; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); nb. 4; (1995); p. 459 - 464 View in Reaxys

O O

Rx-ID: 22153719 View in Reaxys 258/276 Yield

Conditions & References Reaction Steps: 2 2: bei der Destillation Douetteau; Bulletin de la Societe Chimique de France; vol. <4> 11; (1912); p. 653

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View in Reaxys HO

Rx-ID: 41548 View in Reaxys 259/276 Yield

Rx-ID: 606953 View in Reaxys 260/276 Yield

Conditions & References Behal; Tiffeneau; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 132; (1901); p. 563; Bulletin de la Societe Chimique de France; vol. <4>3; (1908); p. 302,305 View in Reaxys

Rx-ID: 625066 View in Reaxys 261/276 Yield

O O

O I

Rx-ID: 627097 View in Reaxys 262/276 Yield

Rx-ID: 1362932 View in Reaxys 263/276 Yield

Conditions & References (i) nBuLi, polystyrene, (ii) /BRN= 639167/, Multistep reaction Heitz,W.; Michels,R.; Angewandte Chemie; vol. 84; (1972); p. 296 - 297 View in Reaxys

H O

Mes2BCHLiMe

Rx-ID: 6674655 View in Reaxys 264/276

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Yield

Conditions & References Yield given. Multistep reaction Pelter, Andrew; Buss, Dieter; Colclough, Eamon; Journal of the Chemical Society, Chemical Communications; nb. 4; (1987); p. 297 - 299 View in Reaxys

O OH

Rx-ID: 623861 View in Reaxys 265/276 Yield

Conditions & References Erhitzen des Reaktionsprodukts im Vakuum auf 150-170grad Pauly; v. Buttlar; Justus Liebigs Annalen der Chemie; vol. 383; (1911); p. 278 View in Reaxys Claisen; Eisleb; Justus Liebigs Annalen der Chemie; vol. 401; (1913); p. 44 View in Reaxys Douetteau; Bulletin de la Societe Chimique de France; vol. <4>; nb. 11; (1912); p. 655 View in Reaxys With diethyl ether, Erhitzen des Reaktionsproduktes unter vermindertem Druck auf 150-170grad Pauly; v. Buttlar; Justus Liebigs Annalen der Chemie; vol. 383; (1911); p. 278 View in Reaxys Claisen; Eisleb; Justus Liebigs Annalen der Chemie; vol. 401; (1913); p. 44 View in Reaxys Douetteau; Bulletin de la Societe Chimique de France; vol. <4> 11; (1912); p. 653 View in Reaxys

O OH

Rx-ID: 623902 View in Reaxys 266/276 Yield

bentonite

Rx-ID: 5802260 View in Reaxys 267/276 Yield

Conditions & References T= 400 °C

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Levi; Nicholls; Industrial and Engineering Chemistry; vol. 50; (1958); p. 1005 View in Reaxys

Na + O

O–

O O

Rx-ID: 659669 View in Reaxys 268/276 Yield

Conditions & References T= 150 °C Gattermann; Eggers; Chemische Berichte; vol. 32; (1899); p. 290 View in Reaxys

Rx-ID: 605836 View in Reaxys 269/276 Yield

Conditions & References Behal; Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 316; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 597 View in Reaxys Behal; Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 316; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 597 View in Reaxys

ethyl magnesium halide (excessive)

O O

polymer(ic) anethole

Rx-ID: 6218767 View in Reaxys 270/276 Yield

Rx-ID: 583946 View in Reaxys 271/276 Yield

Mg+ I–

Rx-ID: 605856 View in Reaxys 272/276 Yield

Conditions & References mehrstuendiges Erhitzen und nachfolgende Zers. mit verd.Schwefelsaeure Behal; Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 316; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 597 View in Reaxys

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Rx-ID: 625245 View in Reaxys 273/276 Yield

O O

Mg O

Rx-ID: 627256 View in Reaxys 274/276 Yield

Conditions & References mit einem Ueberschuss Behal; Tiffeneau; Bulletin de la Societe Chimique de France; vol. <4> 3; (1908); p. 316; Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences; vol. 141; (1905); p. 597 View in Reaxys OH

polymer(ic) o-propenyl-phenol (?)

Rx-ID: 6218787 View in Reaxys 275/276 Yield

Conditions & References Pauly; v. Buttlar; Justus Liebigs Annalen der Chemie; vol. 383; (1911); p. 278 View in Reaxys HO O

trimer(ic) 2-propenyl-phenol

Rx-ID: 6220753 View in Reaxys 276/276 Yield

Conditions & References Erhitzen des nach der Hydrolyse isolierten Reaktionsprodukts auf 130grad Grumez; Annales de Chimie (Cachan, France); vol. <11> 10; (1938); p. 378,387 View in Reaxys

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