Potassium Carbonate → (5,6-Dichloropyridin-3-yl)methanol

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Reaction Steps

At 0° C., 859 ml (859 mmol) of a 1 M solution of boran/tetrahydrofuran complex in tetrahydrofuran are added dropwise to 110 g (573 mmol) of 5,6-dichloro-nicotinic acid in 250 ml of tetrahydrofuran. The mixture is warmed to room temperature and stirred at this temperature for 3 hours. After cooling to 0° C., the reaction mixture is made alkaline using saturated aqueous potassium carbonate solution, most of the tetrahydrofuran is removed using a rotary evaporator and the residue is extracted repeatedly with ethyl acetate. The combined organic phases are washed with water and saturated in aqueous sodium chloride solution and dried over sodium sulphate. The organic phase is concentrated under reduced pressure and the residue is purified by column chromatography on silica gel (silica gel 60-Merck, particle size: 0.04 to 0.063 mm) using the molar phase mixture ethyl acetate:cyclohexane (1:2), giving 62 g (61% of theory) of (5,6-dichloropyridin-3-yl)methanol.

Provenance & Evidence