Hydrochloric Acid → (1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanol

HRID 129115Notes

Reaction equation

HRID 129115 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12]([O:14]C(=O)C2C=CC=CC=2)[CH3:13])[CH2:11][O:10]1.C[O-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([C@@H:12]([OH:14])[CH3:13])[CH2:11][O:10]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10709605[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoateHCID 10942334Sodium Methoxide

Product 1

HCID 10631861(1S)-[(2R)-(2,4-difluorophenyl)-2-oxiranyl]ethanolYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

[(1S)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]ethyl]benzoate (15.9 g) was dissolved in 800 ml of methanol. 28% Methanolic solution (12.9 ml) of sodium methylate was added with ice cooling and the reaction solution was stirred at room temperature for 6 hours. To the reaction solution was added 63.2 ml of 1N hydrochloric acid and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluate; hexane:ethyl acetate=6:1 to 2:1) to give 9.7 g of (1S)-1-[(2R)-2-(2,4-difluorophenyl)- 2-oxiranyl]ethanol as a colorless oil.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customThe residue was purified by silica gel chromatography (eluate; hexane:ethyl acetate=6:1 to 2:1)

Sources & evidence

ORD record
ord-2a3c7a8c66704997aac0826c2d989ec8
Source dataset
uspto-grants-1995_11
Patent number
US05466820

Reaction notes

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