2-Chloropyridine → HCID 19854561, compound

Participants

Reaction Steps

A solution of 4 chloropyridine (2.50 g) in tetrahydrofuran is chilled to 40° . Phenyl chloroformate (2.8 ml) is then added dropwise, and the resulting thick slurry is warmed to -20° . A solution of 1M benzylmagnesium chloride in tetrahydrofuran (22 ml) is added dropwise, taking care to maintain the temperature below 0°. Upon completion of the addition, the cooling bath is removed and the reaction allowed to warm to room temperature. The reaction is then treated with 50% saturated aqueous ammonium chloride and diluted with diethyl ether (200 ml). The organic phase is washed with 1N hydrochloric acid (50 ml) and 1M disodium hydrogen phosphate (50 ml). Drying and concentration of the organic phase affords the intermediate 2-benzyl-1-carbophenoxy-1,2-dihydropyridine as an oil (7.2 g).

Provenance & Evidence