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

Participants

Reaction Steps

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)).

Provenance & Evidence