2,3-Dimethyl-2-phenyloxirane → HCID 67524986, compound
Reaction equation
[CH3:1][C@H:2]1[O:4][C@@:3]1([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:5].[CH3:12][SH:13].[Na]>CO>[CH3:12][S:13][C@H:2]([CH3:1])[C@@:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([OH:4])[CH3:5]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a solution of trans-2,3-dimethyl-2-phenyloxirane (14 g, 76 mmol) in methanol (100 mL) was added 15% aqueous sodium methyl mercaptan solution (61 mL, 190 mmol) under nitrogen atmosphere at room temperature, and the mixture was warmed to 60° C. and stirred for 2 hours. The mixture was concentrated under reduced pressure, and the residue was extracted twice with diethyl ether (50 mL), sequentially washed with water (50 ml) and saturated aqueous sodium chloride solution (50 mL), and dried over sodium sulfate. The resultant mixture was filtrated and the solvent was evaporated to give the title compound (16 g, yield 99%) as a colorless oil.
Workup
- concentrationThe mixture was concentrated under reduced pressure
- extractionthe residue was extracted twice with diethyl ether (50 mL)
- washsequentially washed with water (50 ml) and saturated aqueous sodium chloride solution (50 mL)
- dry with materialdried over sodium sulfate
- filtrationThe resultant mixture was filtrated
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-770047fb126646ac98526d685cb8f5f5
- Source dataset
- uspto-grants-2008_04
- Patent number
- US07351825B2
Reaction notes
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