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

HRID 37465ノート

反応式

HRID 37465 の反応式
[Na].[C:2]([O:9][CH2:10][CH3:11])(=[O:8])[C:3]([O:5]CC)=O.[C:12]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:14])[CH3:13]>C(O)C>[C:12]([CH2:13][C:3](=[O:5])[C:2]([O:9][CH2:10][CH3:11])=[O:8])(=[O:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

参加物

5

反応物 3

HCID 7268Diethyl OxalateHCID 7410AcetophenoneHCID 5360545Sodium

生成物 1

HCID 2265032,4-Dioxo-4-phenyl-butyric acid ethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

In 560 ml of ethanol was dissolved 25 g (1.08 eq.) of sodium and a mixture of 135.6ml (146 g; 1 mol) of diethyl oxalate and 116.7 ml (120 g; 1 mol) of acetophenone was added thereto dropwise at 40° C. One hour later, reflux was begun and it was continued for 30 minutes. The solvent was distilled off. The residue was neutralized with sulfuric acid (55 g/water 200 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. Thereafter, the solvent was distilled off, and the residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane 1:1), to give colorless plates. The crystals were recovered by filtration with ethyl acetate/hexane. Yield: 114.6 g.

後処理

  1. additionwas added
  2. customdropwise at 40° C
  3. temperatureOne hour later, reflux
  4. distillationThe solvent was distilled off
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materiala saturated aqueous solution of sodium chloride, and dried over magnesium sulfate
  8. distillationThereafter, the solvent was distilled off
  9. customthe residue was purified by silica gel column chromatography (eluent: dichloromethane/hexane 1:1)
  10. customto give colorless plates
  11. filtrationThe crystals were recovered by filtration with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-f711d3437ac74f85b47876be8d6e5fe7
出典データセット
uspto-grants-1995_05
特許番号
US05420275

反応ノート

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