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

HRID 482043Notes

Reaction equation

HRID 482043 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, and 12.9 ml of 28% methanolic solution of sodium methylate was added thereto with ice cooling. The reaction solution was stirred for six hours at room temperature. 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 (eluent: 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 (eluent: hexane/ethyl acetate=6/1 to 2/1)

Sources & evidence

ORD record
ord-228545160b284bb2bd680b98b59f0dec
Source dataset
uspto-grants-1998_08
Patent number
US05792780

Reaction notes

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