Sodium borohydride → 1-(6-Bromopyridin-2-yl)ethane-1,2-diol

Participants

Reaction Steps

A solution of 1-(6-bromopyridin-2-yl)-2-hydroxyethanone (2.2 g, 10.18 mmol) in ethanol (127 mL) was charged with sodium borohydride (0.385 g, 10.18 mmol). After 30 minutes, the reaction was concentrated to dryness and then partitioned between ethyl acetate (50 mL) and 3:1 saturated aqueous sodium bicarbonate:water (25 mL). The layers were separated and the organic layer was washed with brine (25 mL), dried over sodium sulfate, filtered, and concentrated to afford the title compound. 1H NMR (600 MHz, DMSO): δ 7.69 (m, 1H), 7.46 (m, 2H), 5.50 (d, J=5.0 Hz, 1H), 4.69 (m, 1H), 4.49 (m, 1H), 3.61 (m, 1H), 3.46 (m, 1H).

Provenance & Evidence