Water → 4-({[Tert-butyl(diphenyl)silyl]oxy}methyl)pyridine-2-carbaldehyde

Participants

Reaction Steps

To a solution of 2-bromo-4-({[tert-butyl(diphenyl)silyl]oxy}methyl)pyridine (8.50 g) in diethyl ether (80 mL) was slowly added a 1.6M n-butyllithium hexane solution (13.0 mL) at −78° C. The reaction mixture was stirred for 30 min, a solution of N,N-dimethylformamide (1.85 mL) in tetrahydrofuran (20 mL) was added, and the mixture was warmed to room temperature and stirred for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (2.16 g, yield 29%) was obtained as a colorless amorphous solid from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 376 (MH+).

Provenance & Evidence