1-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone → HCID 10670941, compound

Participants

Reaction Steps

1-[4-(1,1,2,2-Tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (1.42 g) was dissolved in 10 ml of 1-methyl-2-pyrrolidone, to which 60% sodium hydride in oil (0.198 g) was added. The mixture was stirred at room temperature for 30 minutes. The reaction solution was ice-cooled and added dropwise under nitrogen atmosphere over the period of 10 minutes to a solution of 1.8 g of (2S)-2', 4'-difluoro-2-trifluoromethanesulfonyloxypropiophenone in 50 ml of tetrahydrofuran which was cooled to -40° C. Then, the reaction temperature was raised to -20° C. over the period of 20 minutes and the reaction solution was stirred for 10 minutes. The reaction solution was diluted with 3.5 ml of acetic acid and 70 ml of ethyl acetate, washed with water (40 ml×2), 0.5N-hydrochloric acid (40 ml×2) and 40 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: 300 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.08) to give 0.94 g of 1-[(1R)-2-(2,4-difluorophenyl)-2-oxo-1-methylethyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone as a pale yellow viscous substance. The product was crystallized from a mixture of diisopropyl ether and hexane to give colorless powdery crystals.

Provenance & Evidence