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

HRID 2299634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299634
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 12347320(2S)-1-phenylthio-2,3-epoxypropaneAusbeute 78,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-0b1a708475ef44d8b727397db62c6141
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495546B1

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