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

HRID 1351848Notes

Reaction equation

HRID 1351848 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-274d2709830448488a61982f970cb270
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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