Sodium Hydroxide → (S)-(4-Fluorophenyl)oxirane
Reaction equation
[OH-].[Na+].Cl[CH2:4][C@H:5]([C:7]1[CH:12]=[CH:11][C:10]([F:13])=[CH:9][CH:8]=1)[OH:6]>C(OCC)C>[F:13][C:10]1[CH:11]=[CH:12][C:7]([C@H:5]2[CH2:4][O:6]2)=[CH:8][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1.6 M aqueous sodium hydroxide solution (50 ml) was added to a solution of 2-chloro-(1S)-1-(4-fluorophenyl)ethanol (10.4 g) in diethyl ether (40 ml), and the mixture was stirred at room temperature for 5 hrs. The organic layer was separated and the aqueous layer was extracted with diethyl ether. The combined organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give (2S)-2-(4-fluorophenyl)oxirane (8.28 g) as a colorless oil.
Workup
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with diethyl ether
- washThe combined organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was evaporated
Sources & evidence
- ORD record
- ord-a2c1a25bbfbd460b93acd43a194b2fd2
- Source dataset
- uspto-grants-2011_08
- Patent number
- US07994315B2
Reaction notes
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