Sodium borohydride → (5-(Phenylethynyl)pyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-(Phenylethynyl)nicotinaldehyde (7.0 g, 33.8 mmol) in ethanol (150 mL), immersed in a room temperature bath to moderate any potential exotherm, was added sodium borohydride (0.639 g, 16.9 mmol) in one portion. After 30 min at room temperature, the reaction was cooled to 0° C. and quenched by the cautious addition of saturated ammonium chloride. The reaction was concentrated and partitioned between water and ether. The aqueous was extracted with ether (2×). The organics were washed with brine, dried over magnesium sulfate, and concentrated to give a faint yellow solid. Material was used without purification. 1H NMR (CDCl3) δ: 8.39-8.81 (m, 2H), 7.88 (s, 1H), 7.51-7.61 (m, 2H), 7.34-7.44 (m, 3H), 4.77 (s, 2H), 3.21 (br. s., 1H). 13C NMR (CDCl3) δ: 151.1, 147.1, 137.3, 131.8, 129.0, 128.6, 122.5, 93.0, 85.9, 62.3. Mass spec.: 210.1 (MH)+.

Provenance & Evidence