Water → 5-(1,3-Dioxolan-2-yl)picolinaldehyde

Participants

Reaction Steps

To a solution of 2-bromo-5-(1,3-dioxolan-2-yl)pyridine (9.60 g) in tetrahydrofuran (150 mL) was slowly added a 1.6M n-butyllithium hexane solution (28.7 mL) at −78° C. The reaction mixture was stirred for 30 min, N,N-dimethylformamide (3.9 mL) in tetrahydrofuran (50 mL) was added, and the mixture was warmed to room temperature and stirred for 30 min. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate solution. 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 (2.70 g, yield 36%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio). MS: 180 (MH+).

Provenance & Evidence