2-Acetylthiophene → Rac-alpha-hydroxy-alpha-propyl-gamma-oxo-2-thiophenebutyric acid

HRID 1197806

反応式

HRID 1197806 の反応式
[OH-].[K+].[CH3:3][CH2:4][CH2:5][C:6]([C:8]([OH:10])=[O:9])=[O:7].[C:11]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)(=[O:13])[CH3:12]>O.C(O)C>[OH:7][C:6]([CH2:5][CH2:4][CH3:3])([CH2:12][C:11](=[O:13])[C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)[C:8]([OH:10])=[O:9]

参加物

6

反応物 3

HCID 69202-AcetylthiopheneHCID 14797Potassium HydroxideHCID 745632-Oxovaleric acid

生成物 1

HCID 54564597Rac-alpha-hydroxy-alpha-propyl-gamma-oxo-2-thiophenebutyric acid収率 41.3%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

11.2 g (200 mmol) of potassium hydroxide in 75 ml of water are added at 0° dropwise to a suspension of 11.6 g (100 mmol) of 2-oxo-n-valeric acid and 12.6 g (100 mmol) of 2-acetylthiophene in 75 ml of ethanol and the suspension is held at 0° for 48 hours. After evaporation of the ethanol the residue is made acidic with 25% hydrochloric acid and extracted three times with ethyl acetate. The combined ethyl acetate extracts are dried, filtered and evaporated. After chromatography on silica gel using a 5:1 mixture of methylene chloride and methanol as the eluent and crystallisation from ether there are obtained 10.0 g (41%) of rac-α-hydroxy-α-propyl-γ-oxo-2-thiophenebutyric acid as a colorless powder, melting point 128°-131°, MS: 197 (M-COOH)+.

後処理

  1. customAfter evaporation of the ethanol the residue
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined ethyl acetate extracts are dried
  4. filtrationfiltered
  5. customevaporated
  6. additionAfter chromatography on silica gel using a 5:1 mixture of methylene chloride and methanol
  7. customas the eluent and crystallisation from ether

出典と根拠

ORDレコード
ord-a9394a4307f54d3e8de32a04755f31c9
出典データセット
uspto-grants-1994_01
特許番号
US05278161

関連ノート

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