Methyl iodide → HCID 11747380, compound

Participants

Reaction Steps

A mixture of Ag2CO3 (7.17 g, 26.2 mmol), pyridone 3 (5.4 g, 21.9 mmol), and iodomethane (8.0 mL, 131 mmol) in 200 mL of CHCl3 was refluxed in the dark with stirring. After cooling, filtration, and concentration, the residue was purified by flash chromatography with 25% ethyl acetate in hexanes as the eluent to afford 5.14 g (90%) of 4a: IR (neat) 2953, 1589, 1487, 830 cm-1 ; 1H NMR δ7.22 (d, 1H, J=8.2 Hz), 6.52 (d, 1H, J=8.2 Hz), 5.80 (m, 1H), 5.03 (m, 2H), 4.01 (m, 4H), 3.89 (s, 3H), 3.11 (m, 1H), 2.96 (m, 2H), 2.80 (dd, 1H, J=16.0, 2.4 Hz), 2.50 (m, 1H), 2.06 (m, 1H), 1.80 (dd, 1H, J=13.2, 10.9 Hz); 13C NMR δ162.0, 154.5, 139.7, 137.1, 121.6, 116.3, 108.1, 107.9, 64.5, 64.4, 53.1, 39.4, 38.1, 38.0, 36.6; MS m/z 261 (M+), 246, 220, 174, 148.

Provenance & Evidence