Water → (1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanol

HRID 731002Notes

Reaction equation

HRID 731002 reaction equation
Cl[CH2:2][C@@:3]([C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=1[F:15])([OH:7])[C@H:4]([OH:6])[CH3:5].C[O-].[Na+].O>CO>[O:7]1[C@@:3]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][C:9]=2[F:15])([C@H:4]([OH:6])[CH3:5])[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 67176026(2S,3R)-1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

Product 1

HCID 10536015(1R)-1-[(2R)-2-(2,4-difluorophenyl)-2-oxiranyl]ethanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.12 g (0.45 mmol) of (2S,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol in 3 mL of methanol was cooled in ice, and 0.12 g (0.6 mmol) of a 28% solution of NaOMe in methanol was added. Reaction was performed for 2 hours, and 10 mL of water was added to stop the reaction. Extraction was performed with ethylacetate (10 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain a crude product. The resulting crude product was purified by column on silica gel to obtain 0.09 g of the title compound (yield: 96%).

Workup

  1. customReaction
  2. customthe reaction
  3. extractionExtraction
  4. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  5. customto obtain a crude product
  6. customThe resulting crude product was purified by column on silica gel

Sources & evidence

ORD record
ord-f37300405f284df38cce66529924a59a
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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