Methanol → (6-(Benzyloxy)pyridin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Lithium borohydride (517 mg, 23.5 mmol) and MeOH (752 mg, 23.5 mmol) were added to a solution of benzyl 6-(benzyloxy)nicotinate (5 g, 15.7 mmol) in THF (50 mL) under N2 at 0° C. The mixture was stirred at 70° C. for 2 hours. The mixture was diluted with saturated aqueous ammonium chloride solution and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/EtOAc) to afford (6-(benzyloxy)pyridin-3-yl)methanol. MS ESI calc'd. for C13H14NO2 [M+H]+ 216. found 216. 1H NMR (400 MHz, DMSO-d6) δ 8.11 (d, J=2.0 Hz, 1H), 7.69-7.67 (m, 1H), 7.45-7.33 (m, 5H), 6.86 (d, J=8.4 Hz, 1H), 5.35 (s, 2H), 5.23-5.20 (m, 1H), 4.52-4.44 (m, 2H).

Provenance & Evidence