Butanal → HCID 23028680, compound

Participants

Reaction Conditions

Reaction Steps

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 7.01 ml, 11.0 mmol) was added to a tetrahydrofuran (50 ml) solution of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (3.03 g, 10.0 mmol) obtained in Example 5 and the mixture was stirred at −78° C. for 1 hour. Butanal (1.08 ml, 12.0 mmol) was added dropwise to the reaction mixture. The mixture was stirred for 15 hours while elevating its temperature to room temperature. After cooling to 0° C. and addition of a saturated aqueous ammonium chloride solution, the mixture was extracted with diethyl ether. The extracts were combined, washed successively with water and brine, dried over MgSO4, and then concentrated. The solid thus precipitated was collected by filtration and washed with hexane. The filtrate and washing with hexane were combined, followed by concentration. The residue was purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane) as a high-polarity isomer to yield a colorless solid. The resulting colorless solid was recrystallized from hexane, whereby the title compound (396 mg, 11%) was obtained as colorless needle crystals.

Provenance & Evidence