Hydrochloric Acid → [6-(3-Chloro-phenyl)-pyridin-2-yl]-methanol

Participants

Reaction Steps

399 mg (10.50 mmol) lithium aluminium hydride were given to 18 ml tetrahydrofuran (THF) and stirred at room temperature (r. t.) for 10 min. A solution of 1.30 g (5.25 mmol) 6-(3-Chloro-phenyl)-pyridine-2-carboxylic acid methyl ester in 18 ml THF was added drop by drop at 0° C. within 15 min., and the mixture stirred for 2 h at 0° C. 32 ml brine were added slowly at 0° C. and stirred continued for 2 h. The mixture was adjusted to pH=5 by slowly addition of conc. HCl. A formed salt precipitate was isolated by filtration and washed with THF. The combined THF-solutions were evaporated, the residue extracted twice with ethyl acetate, the organic phase dried (sodium sulphate) and evaporated. Chromatography on silica (eluent: ethyl acetate/n-heptane 1:1) gave 0.45 g (35%) of [6-(3-Chloro-phenyl)-pyridin-2-yl]-methanol

Provenance & Evidence