Sodium Hydroxide → (S)-(4-Fluorophenyl)oxirane

HRID 1671471Notes

Reaction equation

HRID 1671471 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]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10012415(alphaS)-alpha-(Chloromethyl)-4-fluorobenzenemethanol

Product 1

HCID 11228840(S)-(4-Fluorophenyl)oxiraneYield 100.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with diethyl ether
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. 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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