Diethyl Ether → HCID 15204724, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3.59 g (0.019 mol) of o-bromobenzyl alcohol in 100 ml of ether cooled to -20° C. was added in portions 4.1 ml (0.0412 mol) of n-butyllithium (10M) in hexane over a 6 min period, and the reaction mixture was stirred 20 min. The above reaction mixture was cooled to -20° C., 3 g (0.021 mol) of 3-methoxy-pyridine-2-carboxaldehyde in 5 ml of THF was added in one portion to the mixture, and the resulting reaction mixture was allowed to warm to room temperature and stirred for 20 min. Ammonium chloride solution (30 ml) was added to the mixture and the mixture was extracted with ethyl acetate (3×50 ml). The organic layer was washed with brine, dried over sodium sulfate, and concentrated. The diol was triturated with 100 ml of ether, filtered, and purified by chromatography on silica gel eluting with 4% methanol/hexane. The solvent was concentrated in vacuo to afford 0.68 g (14.5%) of 2-[1-hydroxy-(2'-hydroxymethyl)benzyl]-3-methoxypyridine (Formula XIII: R1 =3--OCH3 ; R2 =R7 =H), as a white solid, m.p. 138°-140° C.

Provenance & Evidence