Hydrochloric Acid → HCID 55071304, compound

Temperature

-78 °C

19.9 ml (31.89 mmol) of a 1.6N solution of n-butyllithium in hexane were added dropwise to a solution of 6.7 ml (31.89 mmol) of hexamethyldisilazane in 50 ml of tetrahydrofuran at 0° C., and the mixture was stirred for 15 min and then cooled to −78° C. 3.12 ml (31.89 mmol) of ethyl acetate were added, the mixture was stirred for 1 h and, after addition of 5.00 g (26.57 mmol) of 4-trifluoromethylacetophenone, dissolved in 20 ml of tetrahydrofuran, stirred at −78° C. for a further hour. 1N hydrochloric acid was added to the reaction solution, and the phases were separated. The aqueous phase was extracted with ethyl acetate, and the combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8/2) to result in 7.14 g (97% of theory) of the title compound.

1. stirringthe mixture was stirred for 1 h
2. stirringstirred at −78° C. for a further hour
3. customthe phases were separated
4. extractionThe aqueous phase was extracted with ethyl acetate
5. dry with materialthe combined organic phases were dried over sodium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customThe crude product was purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 8/2)

ORD record

ord-7dcffd5663034edfbcb64a9fa1a4d270

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063234B2