Water → (6-Iodopyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

40 g (145 mmol) of ethyl 6-iodonicotinate diluted in 400 mL of ethanol are added dropwise to a solution at 0° C. of 27.3 g (−722 mmol) of sodium borohydride in 270 mL of ethanol. For the addition, the temperature of the reaction mixture is maintained from 2 and 6° C., and then at 0° C. for 1 hour and at room temperature for 20 hours. The reaction is worked up by addition of 200 mL of water, and a white precipitate forms. The reaction mixture is filtered off; the filtrate is evaporated under vacuum to give the product in the form of a yellow paste. The product is placed in 300 mL of diethyl ether and then filtered to give 23.2 g (68%) of (6-iodopyrid-3-yl)methanol in the form of a pale yellow solid.

Provenance & Evidence