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

HRID 731003Notes

Reaction equation

HRID 731003 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].[OH-].[Na+].O.C(#N)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])([CH:4]([OH:6])[CH3:5])[CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 67176026(2S,3R)-1-Chloro-2-(2,4-difluorophenyl)butane-2,3-diol

Product 1

HCID 112178791,2-Epoxy-2-(2,4-difluorophenyl)butan-3-olYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.28 g (1.2 mmol) of (2S,3R)-1-chloro-2-(2,4-difluorophenyl)butane-2,3-diol ((2S,3R)/(2R,3R)=88/12) in 3 mL of methanol was cooled in ice, and 1.4 mL of a 1 M aqueous solution of NaOH was added thereto. Reaction was performed for 1.5 hours, and 10 mL of water was added to stop the reaction. Extraction was performed with ethylacetate (20 mL). After drying over anhydrous sodium sulfate, concentration was performed under reduced pressure to obtain a crude product. The resulting crude product was quantitatively analyzed by HPLC. Thereby, the title compound was obtained in a yield of 95% ((2R,3R)/(2S,3R)=88/12) (HPLC, column: CAPCELL PAK C18 TYPE MG, mobile phase: acetonitrile/20 mM (potassium) phosphate buffer solution (pH=2.5)=2/8, flow rate: 1.0 mL/min, column temperature: 30° C., detector: UV 210 nm, retention time: 28 minutes (2S,3R), 30 minutes (2R,3R)) 1H-NMR (400 MHz, CDCl3) (2R,3R) δ: 1.16 (d, 3H, J=6.1 Hz), 2.80 (d, 1H, J=4.4 Hz), 3.30 (d, 1H, J=4.4 Hz), 4.09 (q, 1H, J=6.1 Hz), 6.80-6.93 (m, 2H), 7.32-7.37 (m, 1H)).

Workup

  1. customReaction
  2. customthe reaction
  3. extractionExtraction
  4. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  5. customto obtain a crude product

Sources & evidence

ORD record
ord-8fa73f9bffce448eb9ea5022e4ad3a6b
Source dataset
uspto-grants-2009_09
Patent number
US07582781B2

Reaction notes

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