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

HRID 1636678Notes

Reaction equation

HRID 1636678 reaction equation
C([O:9][C@H:10]([C@@:12]1([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:16]=2[F:22])[CH2:14][O:13]1)[CH3:11])(=O)C1C=CC=CC=1.Cl>CO.C[O-].[Na+].CO>[F:22][C:16]1[CH:17]=[C:18]([F:21])[CH:19]=[CH:20][C:15]=1[C@:12]1([C@@H:10]([OH:9])[CH3:11])[CH2:14][O:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 10709605[(1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethyl]benzoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23694274Sodium methanolate methanolSolvent

Procedure

[(1S)-1-[(2R)-2-(2,4-Difluorophenyl)-2-oxiranyl]-ethyl] benzoate (15.9 g) was dissolved in methanol (800 ml), to which 28% sodium methylate-methanol solution (12.9 ml) was added at ice-bath temperature and stirred at room temperature for 6 hours. After 1N-hydrochloric acid (63.2 ml) was added thereto, 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 (1S)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol (9.7 g) as a colorless oily substance.

Workup

  1. additionwas added at ice-bath temperature
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe residue was purified by silica gel chromatography (eluent:hexane/ethyl acetate=6/1 to 2/1)

Sources & evidence

ORD record
ord-d9278c3fc1b74fdeb98e94a64d7971f6
Source dataset
uspto-grants-2000_03
Patent number
US06034248

Reaction notes

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