Hydrochloric Acid → HCID 9815793, compound

Participants

Reaction Steps

Into a four-necked flask equipped with a thermometer, a dropping funnel and a stirrer, 4.8 g (0.2 mol) of magnesium flasks and 100 ml of anhydrous tetrahydrofuran were placed, followed by addition of a mixture of 4.0 g (20 mmol) of 1-bromo-3-phenylpropane and 10 ml of anhydrous tetrahydrofuran and a small quantity of iodine, heating of the flask contents to 60° C. and dropwise addition of a mixture of 35.8 g (0.18 mol) of 1-bromo-3-phenylpropane and 90 ml of anhydrous tetrahydrofuran at the same temperature. Thereafter, the mixture was stirred under reflux for 2 hours and then cooled to room temperature. The resulting mixture was added dropwise into a mixture consisting of 31.3 g (0.22 mol) of ethyl trifluoroacetate and 200 ml of anhydrous tetrahydrofuran. Thereafter, the mixture was stirred at -78° C. for 2 hours, then heated gradually to -50° C. and further stirred at the same temperature for 2 hours. Thereafter, 100 ml of 1N hydrochloric acid was added at -50° C., followed by heating to room temperature. The reaction mixture was extracted with 300 ml of ether and the formed organic layer was washed with water, a 5% sodium bicarbonate solution and brine successively in that order, then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (eluent: toluene/hexane (1/4)) to give 20.3 g of 5-phenyl-1,1,1-trifluoropentane-2-one (14-1) in a yield of 47%.

Provenance & Evidence