Acetic Acid → HCID 10646750, compound

Participants

Reaction Steps

1-[4-(2,2,3,3-Tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (4.6 g) was dissolved in 30 ml of 1-methyl-2-pyrrolidone, to which 0.6 g of 60% sodium hydride in oil was added. The mixture was stirred at room temperature for 0.5 hours. The reaction solution was ice-cooled and added dropwise under nitrogen atmosphere over the period of 5 minutes to a solution of 5.3 g of (2S)-2'-fluoro-2-trifluoromethanesulfonyloxypropiophenone in 50 ml of tetrahydrofuran which was cooled to -40° C. Then, the reaction solution was stirred at -40° to -35° C. for 20 minutes. To the reaction solution was added 2 ml of acetic acid. The mixture was diluted with a mixture of 300 ml of ethyl acetate and 150 ml of diisopropyl ether, washed with 80 ml of water, 0.5N-hydrochloric acid (80 ml×2) and 40 ml of an aqueous solution of sodium chloride successively, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 200 g, eluent; hexane:ethyl acetate:acetic acid=2:1:0.03) and crystallized from diisopropyl ether to give 2.6 g of 1-[(1R)-2-(2-fluorophenyl)-2-oxo-1-methylethyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone as colorless powdery crystals.

Provenance & Evidence