Water → HCID 10899632, compound

HRID 731007Notes

Reaction equation

HRID 731007 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.C(OCC)(=O)C>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

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 67174702(2R,3S)-1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

Product 1

HCID 10899632HCID 10899632, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.12 g (0.45 mmol) of (2R,3S)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol in methanol 3 mL 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. Then, 10 mL of water was added to stop the reaction, and extraction was performed with ethyl acetate (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 0.086 g of the title compound (yield: 96%).

Workup

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

Sources & evidence

ORD record
ord-bf5e2fc0a02d4317a61f2b5f3e59dc45
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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