Benzyl Alcohol → Benzyl 6-(benzyloxy)pyridine-3-carboxylate

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.2 g, 30.3 mmol, 60 wt %) was added to a solution of benzyl alcohol (3.28 g, 30.3 mmol) in THF (40 mL). The mixture was stirred at 0° C. under N2 for 1 hour. A solution of benzyl 6-chloronicotinate (5 g, 20.2 mmol) in THF (2 mL) was added to the mixture. The mixture was stirred at 20° C. for 12 hours. The mixture was diluted with saturated 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 benzyl 6-(benzyloxy)nicotinate. MS ESI calc'd. for C20H18NO3 [M+H]+ 320. found 320. 1H NMR (400 MHz, DMSO-d6) δ 8.80 (d, J=2.4 Hz, 1H), 8.22-8.19 (m, 1H), 7.48-7.34 (m, 10H), 6.98 (d, J=8.4 Hz, 1H), 5.43 (s, 2H), 5.35 (s, 2H).

Provenance & Evidence