Sodium hydride → HCID 10527851, compound

Participants

Reaction Steps

1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (6.58 g) was dissolved in 45 ml of 1-methyl-2-pyrrolidone, to which 0.86 g of 60% sodium hydride in oil was added. The mixture was stirred at room temperature for 15 hours. The ice-cooled mixture was added dropwise under nitrogen atmosphere over the period of 15 minutes to a solu- tion of 7.98 g of (2S)-2',4'-difluoro-2-trifluoromethanesulfonyloxypropiophenone in 150 ml of tetrahydrofuran which was cooled to -40° C. After the reaction temperature was raised to -20° C. over the period of 20 minutes, the reaction solution was stirred for 10 minutes. The reaction solution was diluted with 16 ml of acetic acid and 200 ml of ethyl acetate, washed with water (100 ml×2), 0.5N-hydrochloric acid (100 ml×2) and 100 ml of a saturated aqueous solution of sodium chloride successively, and dried over anhydrous magnesium chloride. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography (silica gel: 1 kg, eluent; hexane:ethyl acetate:acetic acid=2:1:0.08) and recrystallized from 20 ml of diisopropyl ether to give 4 g of 1-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone as colorless powdery crystals.

Provenance & Evidence