Dichloromethane → 1-Propargyl-3-methoxypyridine-2-one

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of 3-methoxy-2-pyridinone (1.00 g, 8.00 mmol) in DMF (25 mL), was added propargyl bromide (80 wt % solution in toluene, 1.5 equiv) and K2CO3 (3.313 g, 24 mmol). Reaction mixture was heated to 100° C. After overnight reaction, reaction mixture was partitioned between EtOAc (120 mL) and water (100 mL). Organic layer was separated and washed repeatedly with water (7×100 mL) and brine (1×60 mL). Organic layer was dried on Na2SO4 and evaporated under vacuo to yield dark brown crude product. Column chromatography using gradient CH2Cl2:Acetone (max 20%) gave pure 150 (0.79 g, 60%) as a slightly brownish solid. 1H NMR (CDCl3, 400 MHz) δ 2.36 (1H, t, J=2.8), 3.67 (3H, m), 4.66 (1H, d, J=2.8), 6.05 (1H, t, J=7.2), 6.50 (1H, dd, J=1.6, 7.2), 7.11 (1H, dd, J=1.6, 6.8); 13C NMR (CDCl3, 100 MHz) δ 37.2, 55.5, 74.6, 77.3, 104.8, 112.0, 126.3, 149.4, 157.1. HRMS (EI) calcd for C9H9NO2 [M]+ 163.0633. found 163.0636

Provenance & Evidence