Oxalyl chloride → (2,6-Dichloropyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dichloronicotinic acid (10 g) in MeOH (300 mL) was added oxalyl chloride (5.5 mL) dropwise at 0° C. The mixture was heated to 60° C. for a couple of hours until reaction complete. Upon concentration, the residue was dissolved in ether and added lithium aluminum hydride (2.3 g) slowly at 0° C. The reaction was stirred at 0° C. for 1 h and added water (2.3 mL) dropwise to quench excess lithium aluminum hydride. The resulting mixture was added 15% NaOH (2.3 mL) slowly, water (6.9 mL) and stirred at 0° C. for an additional 1 h. The slush solution was filtered through celite and washed with ether. The filtrate was concentrated to give the title compound (6.5 g).

Provenance & Evidence