Methyl iodide → HCID 20040843, compound

Participants

Reaction Steps

To a mixture of 3 (78 mg, 0.3 mmol), K2CO3 (95 mg, 0.69 mmol), in acetone (50 mL), 1 mL (16 mmol) of MeI was added. The reaction mixture was heated to reflux for 48 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 50 mL water. The mixture was then extracted with EtOAc and the combined organic layer was washed with water, then brine, and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography with hexane/CH2Cl2 (2/1) to provide compound 24 (49 mg, 0.18 mmol, 60% yield) as a yellow oil. 1H NMR (CDCl3, 400 MHz) δ 7.23 (m, 2H), 6.83 (m, 4H), 6.73 (d, J=8.4 Hz, 2H), 6.68 (t, J=7 Hz, 1H), 4.07 (t, J=6.4 Hz, 2H), 3.77 (s, 3H), 3.70 (t, J=6.4 Hz, 2H), 3.47 (q, J=7 Hz, 2H), 1.20 (t, J=7 Hz, 3H); 13C NMR (CDCl3, 100 MHz): δ 153.93, 152.91, 147.62, 129.38, 115.95, 115.40, 114.67, 111.80, 66.01, 55.74, 49.76, 45.59, 12.30; HRMS (ESI, positive) m/z calcd. For C17H22NO2 [M+H]+: 272.1645, found: 272.1646.

Provenance & Evidence