Water → 1,2-Epoxy-2-(2,4-difluorophenyl)butan-3-ol

HRID 731015Notes

Reaction equation

HRID 731015 reaction equation
Cl[CH2:2][C:3]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=1[F:21])([OH:13])[CH:4]([O:6]C(=O)C(C)(C)C)[CH3:5].C[O-].[Na+].O.C(OCC)(=O)C>CO>[O:13]1[C:3]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])([CH:4]([OH:6])[CH3:5])[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10942334Sodium MethoxideHCID 231170411-Chloro-2-(2,4-difluorophenyl)-3-pivaloyloxybutan-2-ol

Product 1

HCID 112178791,2-Epoxy-2-(2,4-difluorophenyl)butan-3-olYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 0.45 g (1.4 mmol) of 1-chloro-2-(2,4-difluorophenyl)-3-(pivaloyloxy)butan-2-ol ((2S,3R)/(2R,3R)=93/7)) in 3 mL of methanol was cooled to 0° C., and 0.33 g (1.7 mmol) of a 28% solution of NaOMe in methanol was added. The reaction was performed for 1 hour and at room temperature for another 16 hours. Then, 5 mL of water was added to stop the reaction, and extraction was performed with ethyl acetate (20 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain 0.31 g of a crude product. The resulting product was purified by column on silica gel to obtain 0.11 g of the title compound (yield: 40%) ((2R,3R)/(2S,3R)=96/4 (the diastereomeric ratio was measured by HPLC under the same HPLC measurement conditions as those in Example 10)).

Workup

  1. customthe reaction, and extraction
  2. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  3. customto obtain 0.31 g of a crude product
  4. customThe resulting product was purified by column on silica gel

Sources & evidence

ORD record
ord-c0e8caaa22f143029484f1e49bae20dd
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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