Diethyl Oxalate → 2,4-Dioxo-4-phenyl-butyric acid ethyl ester

HRID 1093579

反応式

HRID 1093579 の反応式
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[C:10](OCC)(=[O:16])[C:11]([O:13][CH2:14][CH3:15])=[O:12].[H-].[Na+]>CN(C=O)C>[CH2:14]([O:13][C:11](=[O:12])[C:10](=[O:16])[CH2:2][C:1](=[O:3])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:15]

参加物

5

反応物 3

HCID 7268Diethyl OxalateHCID 7410AcetophenoneHCID 24758Sodium hydride

生成物 1

HCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl ester収率 42%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A stirred solution of acetophenone (5 g, 0.0416 mole), diethyl oxalate (7.23 g, 0.0416 mole) in DMF (40 mL) was cooled to 0° C. for 10 minutes. NaH (60% w/w dispersion in oil) (2.0 g, 0.083 mole) was then added, and the resulting mixture was stirred at the same temperature for 30 minutes, then stirred at ambient temperature for 1 hour. The mixture was then heated at 50° C. for 30 minutes. The reaction mixture was quenched with iced water, acidified with aqueous 2.4N HCl solution and the resulting precipitate was isolated by filtration and dried to afford 3.8 g (42%) of 2,4-dioxo-4-phenyl-butyric acid ethyl ester. LCMS: 221.07 (M+1)+, 85.2%.

後処理

  1. stirringstirred at ambient temperature for 1 hour
  2. customThe reaction mixture was quenched with iced water
  3. customthe resulting precipitate was isolated by filtration
  4. customdried

出典と根拠

ORDレコード
ord-ad91d38f50294a4ea3cb7e0f549b7e69
出典データセット
uspto-grants-2012_03
特許番号
US08129376B2

関連ノート

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