Hydrochloric Acid → Methyl 6-(hydroxymethyl)picolinate

Participants

Reaction Steps

To a solution of 2-ethyl 6-methylpyridine-2,6-dicarboxylate (3.0 g, 14.3 mmol) in MeOH (20 mL) and CH2Cl2 (10 mL) was added slowly NaBH4 (1.95 g, 51.6 mmol) in several portions at −40° C. After 10 min, the reaction mixture was stirred at rt for 1 h. To the reaction mixture was added 5 mL of 1 N HCl and the mixture was stirred for 20 min. The solvents were removed in vacuo and the residue was diluted with CHCl3 and saturated aqueous NaHCO3 solution (20 mL). The organic layer was separated, dried over MgSO4, filtered and the filtrate solution was concentrated in vacuo to give the desired compound (2.6 g, 54%) as a white solid. 1H NMR (DMSO-d6) δ 8.02 (t, J=8.0 Hz, 1H), 7.92 (d, J=8.0 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 4.62 (d, J=8.0 Hz, 2H), 3.88 (s, 3H). MS (ESI): 168.1 (M+H)+.

Provenance & Evidence