Sodium Methoxide → (2S)-1-phenylthio-2,3-epoxypropane

HRID 2299634ノート

反応式

HRID 2299634 の反応式
[C:1]1([S:7][CH2:8][C@@H:9]([OH:22])[CH2:10]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+]>C(O)C>[C:1]1([S:7][CH2:8][C@H:9]2[O:22][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 13439563(2S)-3-phenylthio-1-tosyloxy-2-propanol

生成物 1

HCID 12347320(2S)-1-phenylthio-2,3-epoxypropane収率 78.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

Under nitrogen, to a solution of (2S)-3-phenylthio-1-tosyloxy-2-propanol (3.9 g) in ethanol (40 ml) was added 20% sodium methoxide in ethanol (4.7 ml) at 5° C., and the mixture was stirred at the same temperature for 30 minutes. After being filtrated off to remove precipitates, the filtrate was concentrated in vacuo. The residue was dissolved into a mixture of aqueous 0.1N sodium hydroxide and diethyl ether. After separation, the organic layer was successively washed with water and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1 to 10:1) to give (2S)-1-phenylthio-2,3-epoxypropane (1.5 g).

後処理

  1. filtrationAfter being filtrated off
  2. customto remove
  3. customprecipitates
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe residue was dissolved into a mixture of aqueous 0.1N sodium hydroxide and diethyl ether
  6. customAfter separation
  7. washthe organic layer was successively washed with water and brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=20:1 to 10:1)

出典と根拠

ORDレコード
ord-0b1a708475ef44d8b727397db62c6141
出典データセット
uspto-grants-2002_12
特許番号
US06495546B1

反応ノート

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