Benzaldehyde → HCID 90013746, compound

Participants

Reaction Conditions

Reaction Steps

A solution of n-butyllithium in hexanes (2.5 M, 27.9 mL, 0.0698 mol) was added dropwise over a period of 30 min to a solution of N,N-diisopropylamine (9.9 mL, 0.069 mol, 1.2 equiv) in anhydrous THF (40 mL) at −78° C. The resulting mixture was slowly warmed to 5° C. over 30 min, then cooled to −78° C., and a solution of 2-bromo-3-methylpyridine (6.5 mL, 0.058 mol) in anhydrous THF (20 mL) was added dropwise over 45 min and stirred for 1 h. A solution of benzaldehyde (7.1 mL, 0.069 mol) in THF (20 mL) was then added dropwise over 15 min. The resulting solution was gradually warmed to 23° C. The reaction mixture was quenched with saturated aqueous ammonium chloride solution, and extracted with ethyl acetate (2×). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica gel eluting with 25% ethyl acetate in petroleum ether to give the title compound. MS: m/z=280.0 (M+1).

Provenance & Evidence