Potassium Hydroxide → (2S)-2-(2,4-Difluorophenyl)-2-oxiranemethanol

HRID 356813Notes

Reaction equation

HRID 356813 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:21])([CH2:15][O:16]S(C)(=O)=O)[CH2:10]OC(=O)C.[OH-].[K+]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@:9]1([O:21][CH2:10]1)[CH2:15][OH:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 15463466(S)-2-(2,4-difluorophenyl)-1-acetoxy-3-methanesulfonyloxy-2-propanol

Product 1

HCID 10176425(2S)-2-(2,4-Difluorophenyl)-2-oxiranemethanolYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 250 ml of toluene was dissolved 50 g of (S)-2-(2,4-difluorophenyl)-1-acetoxy-3-methanesulfonyloxy-2-propanol and thereto was added 250 ml of 20% aqueous solution of potassium hydroxide and then the resulting liquid was stirred at room temperature for 12 hours. A toluene-layer was separated and the aqueous layer was extracted three times with 100 ml of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate and the solvent was removed. The residue was purified by column chromatography on silica gel to give 21 g of (S)-2-(2,4-difluorophenyl)-2,3-epoxy-1-propanol. The optical purity thereof was determined by HPLC analysis (column: CHIRALPAK AS made by Daicel Chemical Industries, Ltd., eluent: n-hexane/isopropanol=98/2, detection wavelength: 254 nm, flow rate: 1.2 ml/min).

Workup

  1. customA toluene-layer was separated
  2. extractionthe aqueous layer was extracted three times with 100 ml of ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-6c19f36204284494bb3fdbf52e9b3b74
Source dataset
uspto-grants-1998_11
Patent number
US05840553

Reaction notes

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