1H-1,2,4-Triazole → (2R,3S)-2-(2,3-Difluorophenyl)-3-methyl-2-[(1H-1,2,4-triazol-1-yl)methyl]oxirane

Participants

Reaction Steps

3.32 g (48.1 mmol) of 1H-1,2,4-triazole were added to a suspension of 1.84 g (41.1 mmol) of a 55% dispersion of sodium hydride in oil in 30 ml of N,N-dimethylformamide at 0° C. with stirring. After the evolution of hydrogen gas had ceased, a solution of 4.50 g (12 mmol) of (2R,3R)-2-(2,3-difluorophenyl)-1,3-bis(methanesulfonyloxy)-2-butanol [prepared as described in Step 7 (iii) above] in 13 ml of N,N-dimethylformamide was added to the above reaction mixture. This resulting mixture was stirred at 70° C. for 1.5 hours. After cooling, a saturated aqueous ammonium chloride solution was added to the reaction mixture. The reaction product was extracted with ethyl acetate and the organic layer was washed with water three times and with aqueous sodium chloride solution once and then concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel (100 g) column using a 1:1 mixture of ethyl acetate and hexane as the eluant to afford 1.80 g (yield 59%) of the title compound as an oil.

Provenance & Evidence