Hexane → HCID 59750887, compound

Participants

Reaction Steps

A tetrahydrofuran (40 ml) solution of 1-bromo-2,5-difluorobenzene (1.21 ml, 10.7 mmol) was stirred at −78° C., followed by the addition of a hexane solution (8.50 ml, 13.4 mmol) of n-butyl lithium. The reaction mixture was added to a tetrahydrofuran (20 ml) solution of 7-(t-butyldiphenylsilyloxy)heptanal (3.28 g, 8.90 mmol) at −78° C. and the mixture was stirred at the same temperature for 30 minutes. After the temperature of the reaction mixture was elevated to room temperature, diethyl ether was added thereto. The mixture was washed with a saturated aqueous solution of ammonium chloride. The organic layer was then dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, and the fraction obtained from the hexane:ethyl acetate=9:1 eluate was concentrated under reduced pressure, whereby the title compound (3.88 g, 8.04 mmol, 90%) was obtained as a colorless oil.

Provenance & Evidence