m-Formylbenzonitrile → 3-[(5-Ethyl-6-methoxy-2-methylpyridin3-yl)hydroxymethyl]benzonitrile

Participants

Reaction Conditions

Reaction Steps

Butyl lithium (2.5M in hexane, 2.09 mL, 5.22 mmol) is added to a solution of 3-bromo-5-ethyl-6-methoxy-2-methylpyridine (1.0 g, 4.35 mmol) in tetrahydrofuran (10 mL) cooled to −50° C. and the reaction mixture is stirred for 45 min after which 3-cyanobenzaldehyde (0.71 g, 5.44 mmol) is added in two portions. After 1 hr at −50° C., the dry ice/acetone bath is removed, the reaction is warmed to room temperature, quenched with sat. aq ammonium chloride (30 mL) and extracted with ether (40 mL). The extract is dried, filtered, concentrated and the residue is purified by chromatography eluting with cyclohexane and 10 to 15% ethyl acetate. Product containing fractions are combined and concentrated to afford 3-[(5-ethyl-6-methoxy-2-methylpyridin3-yl)hydroxymethyl]benzonitrile (0.69 g, 56% yield).

Provenance & Evidence