Hydrochloric Acid → HCID 9815793, compound

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%.

1. temperatureunder reflux for 2 hours
2. additionThe resulting mixture was added dropwise into a mixture
3. stirringThereafter, the mixture was stirred at -78° C. for 2 hours
4. temperatureheated gradually to -50° C.
5. stirringfurther stirred at the same temperature for 2 hours
6. temperatureby heating to room temperature
7. extractionThe reaction mixture was extracted with 300 ml of ether
8. washthe formed organic layer was washed with water
9. dry with materiala 5% sodium bicarbonate solution and brine successively in that order, then dried over anhydrous magnesium sulfate
10. concentrationconcentrated under reduced pressure

ORD record

ord-1e7a0a9c40a94052bd1da87ed07e91ce

Source dataset

uspto-grants-1993_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05238598