Diethyl 2-oxosuccinate by Asch

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Rx-ID: 646778 Find similar reactions

74%

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Stage #1: oxalic acid diethyl ester With sodium ethanolate in benzene

T=0°C; Inert atmosphere; Stage #2: ethyl acetate in benzene

T=0 - 20°C; 14.5 h; Inert atmosphere;

Riahi, Abdolmajid; Shkoor, Mohanad; Fatunsin, Olumide; Khera, Rasheed Ahmad; Fischer, Christine; Langer, Peter

Organic and Biomolecular Chemistry, 2009 , vol. 7, # 20 p. 4248 - 4251 Title/Abstract Full Text View citing articles Show Details

With diethyl ether; sodium ethanolate

Behandeln in Wasser mit verduennter Schwefelsaeure in Gegenwart von Aether;

Wislicenus

Justus Liebigs Annalen der Chemie, 1888 , vol. 246, p. 324 Full Text View citing articles Show Details

Piutti

Gazzetta Chimica Italiana, 1887 , vol. 17, p. 520 Gazzetta Chimica Italiana, 1890 , vol. 20, p. 169,170 Full Text View citing articles Show Details

Hoechster Farbw.

Patent: DE43847 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 218,597 Full Text Show Details

With diethyl ether; sodium

Behandeln in Wasser mit verduennter Schwefelsaeure in Gegenwart von Aether;

Wislicenus

Justus Liebigs Annalen der Chemie, 1888 , vol. 246, p. 324 Full Text View citing articles Show Details

Piutti

Gazzetta Chimica Italiana, 1887 , vol. 17, p. 520 Gazzetta Chimica Italiana, 1890 , vol. 20, p. 169,170 Full Text View citing articles Show Details

Hoechster Farbw.

Patent: DE43847 ; Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 1, p. 218,597 Full Text Show Details

With sodium

Graf; Liu

Archiv der Pharmazie und Berichte der Deutschen Pharmazeutischen Gesellschaft, 1967 , vol. 300, # 4 p. 348 - 353 Title/Abstract Full Text View citing articles Show Details

With C2H6O*Na(1+) in diethyl ether Heatingovernight;

Campaigne, E.; McLaughlin, Astley R.

Journal of Heterocyclic Chemistry, 1983 , vol. 20, p. 623 - 628 Title/Abstract Full Text Show Details

With sodium ethanolate in diethyl ether

Nepveu, Francoise; Gaultier, Nicolas; Korber, Nikolaus; Jaud, Joel; Castan, Paule

Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1995 , # 24 p. 4005 - 4014 Title/Abstract Full Text View citing articles Show Details

With sodium in ethanol

T=0 - 40°C; 3 h; Inert atmosphere;

Hu, Bing C.; Zhou, Wei Y.; Liu, Zu L.; Cai, Chao J.; Xu, Shi C.

Journal of Porphyrins and Phthalocyanines, 2010 , vol. 14, # 1 p. 89 - 100 Title/Abstract Full Text View citing articles Show Details

With sodium hexamethyldisilazane in tetrahydrofuran

T=-78 - 0°C;

Barawkar, Dinesh A.; Bandyopadhyay, Anish; Deshpande, Anil; Koul, Summon; Kandalkar, Sachin; Patil, Pradeep; Khose, Goraksha; Vyas, Samir; Mone, Mahesh; Bhosale, Shubhangi; Singh, Umesh; De, Siddhartha; Meru, Ashwin; Gundu, Jayasagar; Chugh, Anita; Palle, Venkata P.; Mookhtiar, Kasim A.; Vacca, Joseph P.; Chakravarty, Prasun K.; Nargund, Ravi P.; Wright, Samuel D.; Roy, Sophie; Graziano, Michael P.; Cully, Doris; Cai, Tian-Quan; Singh, Sheo B.

Bioorganic and Medicinal Chemistry Letters, 2012 , vol. 22, # 13 p. 4341 - 4347 Title/Abstract Full Text View citing articles Show Details

With sodium hydride in tetrahydrofuran; ethyl acetate

T=15 - 65°C; 3 h; Hide Experimental Procedure

MERCK SHARP and DOHME CORP.; BARR, Kenneth, Jay; SCOTT, Mark, E.; THOMPSON, Christopher, F.; ANTHONY, Neville; CAMMARANO, Carolyn, Michelle; BAKSHI, Raman, Kumar; MOHANTY, Subhendu, Kumar; KORAPALA, Chandra, Sekhar; LATTHE, Prashant, R.; KAMBAM, Vyjayanthi, N.; SARKAR, Sujit, Kumar; THATAI, Jayanth, Thiruvellore

Patent: WO2015/50798 A1, 2015 ; Location in patent: Page/Page column 59; 60 ; Title/Abstract Full Text Show Details

A:Step A Diethyl 2-oxosuccinate (11a)

Step A Diethyl 2-oxosuccinate (11a); To a solution of sodium hydride (14 g, 60percentw/w, 580 mmol) in THF at 65°C; a solution of diethyl oxalate (43 g, 295 mmol) in ethyl acetate (20 g, 295 mmol) and was added drop wise using an addition funnel for about 2h until the reaction mixture turned pale yellow. The reaction mixture was slowly brought to room temperature and stirred for additional lh. The reaction mixture was cooled to 0°C and acidified with concentrated H2SO4 until pH 3. The reaction mixture was filtered through a celite bed and concentrated under reduced pressure to get 11a as a pale yellow liquid. 38 g

Stage #1: ethyl acetate With sodium ethanolate in tetrahydrofuran

1 h; Reflux; Stage #2: oxalic acid diethyl ester in tetrahydrofuran

4 h; Reflux; Hide Experimental Procedure

Patent: CN106854181 A, 2017 ; Location in patent: Paragraph 0020-0022 ; Title/Abstract Full Text Show Details

1.1:Synthesis of diethyl oxaloacetate

30 g of ethyl acetate was added to 400 ml of anhydrous tetrahydrofuran,46 g of sodium ethoxide was added, heated under reflux for 1 hour,Cooled to room temperature, 50 g of diethyl oxalate was added, stirred for 4 hours under reflux,Concentrated and then ethyl acetate and water were added, separated, dried and concentrated, and the residue was separated on column to give 38 g of diethyl oxaloacetate. 38 g

Stage #1: ethyl acetate With sodium ethanolate in tetrahydrofuran

1 h; Reflux; Stage #2: oxalic acid diethyl ester in tetrahydrofuran

4 h; Hide Experimental Procedure

1.1:(1) Synthesis of diethyl oxaloacetate

Hunan Huateng Pharmaceutical Co., Ltd.; Deng Zeping; Li Shuyun

Patent: CN106749039 A, 2017 ; Location in patent: Paragraph 0021; 0022 ; Title/Abstract Full Text Show Details

30 g of ethyl acetate was added to 400 ml of anhydrous tetrahydrofuran, and 46 g of sodium ethoxide was added, followed by heating under reflux for 1 hour,But further to 50 g of diethyl oxalate, stirred for 4 hours, concentrated and then added with ethyl acetate and water, separated, dried and concentrated. The residue was separated on column to give 38 g of diethyl oxaloacetate.

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Rx-ID: 43839153 Find similar reactions

With sodium hydride in toluene

Reflux;

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Son, Jeong-Yu; Kim, Jonghye; Han, Sang Hoon; Kim, Sung Hong; Lee, Phil Ho

Organic Letters, 2016 , vol. 18, # 20 p. 5408 - 5411 Title/Abstract Full Text View citing articles Show Details

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With water; platinum (II) chloride in methanol

T=60°C;

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Rx-ID: 38411818 Find similar reactions

Chen, Qian; Zhang, Changyuan; Wen, Chunxiao; Fang, Jin; Du, Zhiyun; Wu, Dongling

Catalysis Communications, 2014 , vol. 56, p. 101 - 105 Title/Abstract Full Text View citing articles Show Details

Synthesize Find similar With sulfuric acid in diethyl ether; water

Hide Experimental Procedure

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Patent: WO2007/20502 A2, 2007 ; Location in patent: Page/Page column 27 ; Title/Abstract Full Text Show Details

Rx-ID: 25685445 Find similar reactions

Preparation of Intermediate ethyl 5-(2-chlorophenyl)-1-(4-chlorophenyl)-3-hvdroxy-2-oxo-2,5- dihydro- 1 H-pyrrole-4-carboxylate (l-3a):l-3a A solution of 20.0 g (142 mmol) of 2- chlorobenzaidehyde and 18.2 g (142 mmol) of 4- chloroaniline in 200 ml of absolute ethanol was stirred at room temperature for 16 hours. The solvent was evaporated, the residue was triturated with i-PrOH and collected by filtration to give 33.7 g (95percent) of imine.A solution of 31.1 g (148 mmol) of diethyloxalacetate sodium salt in water was layered with ether and acidified with concentrated sulfuric acid. After agitation, the layers were separated and the aqueous phase extracted twice more with ether. The combined organic layers were dried (magnesium sulfate) and filtered. The imine prepared above was added to the ether solution of diethyloxalacetate and the mixture stirred at room temperature for 4 days. The solvent was evaporated, the residue was triturated with ether and collected by filtration to give 41.2 g (78percent) of the title compound (K3a). 1 H NMR (CDCI3): δ 1.16 (t, J = 7.1 Hz, 3H), 4.17 (m,2H), 6.39 (s, 1 H), 6.92 (dd, J = 7.6, 1.8 Hz, 1 H), 7.11 -7.27 (m, 4H), 7.35 (dd, J = 7.6, 1.4 Hz, 1 H), 7.50 (m, 2H). A

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With sulfuric acid in water

2 h; Ambient temperature; Yield given;

Ikota; Achiwa; Yamada