Borane → (6-(2-Methoxyethoxy)pyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

6-(2-methoxyethoxy)nicotinic acid (3.94 g 20.0 mmol) was dissolved in anhydrous THF (80 ml) and cooled to 0° C., and stirred under argon while a solution of 1M borane in THF (80 ml) was added over a period of 1 hour. The mixture was allowed to warm to room temperature and left to stir for 4 hours to complete the reaction. The reaction was cooled to 0° C., and quenched by the careful addition of methanol (20 ml total) in small aliquots. The mixture was allowed to stir overnight to complete the quench, then concentrated to dryness in vacuo. The solids were partitioned between ethyl acetate (100 ml) and saturated Na2CO3 (50 ml), and separated, then the aqueous extracted again with ethyl acetate (100 ml). The combined organics were washed with brine (50 ml), then dried (MgSO4) and concentrated in vacuo to give the crude product as clear oil (2.86 g).

Provenance & Evidence