2-Pyridinecarboxaldehyde → HCID 15204724, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 10 g (0.059 mol) of 2,5-dimethoxybenzyl alcohol in 250 ml of ether cooled to -20° C. was added in portions 12.75 ml (0.127 mol) of n-butyllithium (10M) in hexane over a 10 min period, and the reaction mixture was allowed to warm to room temperature and stirred 1 hr. The above reaction mixture was cooled to -20° C., 7.58 g (0.07 mol) of pyridine-2-carboxaldehyde was added to the mixture, and the resulting reaction mixture was allowed to warm to room temperature (a brown precipitate formed) and stirred for 1 hr. Ammonium chloride solution (60 ml) was added, the mixture was extracted with ethyl acetate, the combined organic layer was washed with brine, dried over sodium sulfate, and concentrated. The diol was purified by chromatography on silica eluting with ethyl acetate/hexane (9:1) to afford 1.7 g (10.5%) of 2-[(2',5'-dimethoxy-6'-hydroxymethyl)benzyl]pyridine (Formula XIII: R1 =R7 =H; R2 =2',5'(OCH3)2), as a white solid, m.p. 102°-104° C.

Provenance & Evidence