Butanal → HCID 23028680, compound

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere and at −78° C., n-butyl lithium (a 1.60M hexane solution, 0.688 ml, 1.10 mmol) was added to a tetrahydrofuran (5 ml) solution of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (303 mg, 1.00 mmol) obtained in Example 5. The mixture was stirred at −78° C. for 1 hour. After addition of butanal (0.108 ml, 1.20 mmol), the mixture was stirred at −78° C. for 2 hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The extracts were combined, washed successively with water and brine, dried over MgSO4, and then concentrated. The residue was purified by medium-pressure chromatography on a silica gel column (10% ethyl acetate-hexane) as a low-polarity isomer to yield by a colorless solid. The solid thus obtained was washed with hexane, whereby the title compound (30.5 mg, 8%) was obtained as a colorless solid.

Provenance & Evidence