Water → 5-(2,2-Dimethyl-1,3-dioxolan-4-yl)pyridine-2-carbaldehyde

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Reaction Steps

To a solution of 2-bromo-5-(2,2-dimethyl-1,3-dioxolan-4-yl)pyridine (4.12 g) in diethyl ether (100 mL) was slowly added a 1.6M n-butyllithium hexane solution (10 mL) at −78° C. The reaction mixture was stirred for 30 min, and N,N-dimethylformamide (1.40 g) was added. The reaction mixture was warmed to room temperature over 1 hr, and stirred overnight. 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 (900 mg, yield 27%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). MS: 208 (MH+).

Provenance & Evidence