Hydrogen Peroxide → (2R)-2-(4-methoxyphenyl)propanoic acid

HRID 1896243ノート

反応式

HRID 1896243 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([CH3:25])[C:10](N2[C@@H](CC3C=CC=CC=3)COC2=O)=[O:11])=[CH:5][CH:4]=1.[OH-:26].[Li+].OO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C@@H:9]([CH3:25])[C:10]([OH:11])=[O:26])=[CH:7][CH:8]=1

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 67382847(S)-3-((R)-2-(4-methoxyphenyl)propanoyl)-4-benzyloxazolidin-2-one

生成物 1

HCID 12398858(2R)-2-(4-methoxyphenyl)propanoic acid収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (S)-3-((R)-2-(4-methoxyphenyl)propanoyl)-4-benzyloxazolidin-2-one (1.50 g, 4.42 mmol) in THF (20 ml) was added to a mixture of lithium hydroxide (750 mg, 17.6 mmol) and hydrogen peroxide (0.9 ml, 26.5 mmol, 30% in water). The reaction mixture was stirred at room temperature for 3 h. Then the solvent was evaporated, the residue was acidified with diluted HCl (10 ml) and extracted with DCM (3×50 ml). The combined organic layers was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified by column chromatography over silica gel (60-120 mesh) using ethyl acetate (20%) in petroleum ether as eluent to afford 600 mg (76%) of (R)-2-(4-methoxyphenyl)propanoic acid as colorless liquid.

後処理

  1. customThen the solvent was evaporated
  2. extractionextracted with DCM (3×50 ml)
  3. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude compound was purified by column chromatography over silica gel (60-120 mesh)

出典と根拠

ORDレコード
ord-58a4cfb25192484ba9293b857174225b
出典データセット
uspto-grants-2013_08
特許番号
US08518948B2

反応ノート

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