Methanesulfonyl chloride → Methyl 6-((methylsulfonyloxy)methyl)picolinate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 6-(hydroxymethyl)picolinate (2.6 g, 15.5 mmol) in CH2Cl2 (15 mL) were added methanesulfonyl chloride (1.81 mL, 23.3 mmol) and TEA (5.42 mL, 38.9 mmol) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 h and diluted with CHCl3 and saturated aqueous NaHCO3 solution. The organic layer was separated, washed with brine, dried over MgSO4, filtered, and the filtrate was concentrated to give the desired compound (4.2 g, 85%) as a brown oil. 1H NMR (CDCl3) δ 8.15 (d, J=8.0 Hz, 1H), 7.96 (t, J=8.0 Hz, 1H), 7.12 (d, J=8.0 Hz, 1H), 5.46 (s, 2H), 4.04 (s, 3H), 3.20 (s, 3H). MS (ESI): 246.1 (M+H)+.

Provenance & Evidence