Methyl iodide → HCID 57663228, compound

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil) (112 mg, 2.82 mmol) was added to a solution of 7-fluoro-2,2-dimethyl-2,3-dihydro-4H-1,3-benzoxazin-4-one (0.5 g, 2.56 mmol) in THF (10 mL) at 0° C., under argon then the mixture allowed to warm to RT and methyl iodide (0.18 mL, 2.82 mmol) added. The reaction was stirred at RT for 24 hours, poured into ice/water (50 mL) and extracted into ethyl acetate (50 mL). The organic layer was washed with brine (50 mL), dried (MgSO4), and the solvent removed in vacuo to give a yellow oil which was chromatographed on silica, eluting with 30-60% ethyl acetate in isohexane, to give the desired compound as a colourless oil (0.36 g). 1H NMR δ (CDCl3): 1.65 (s, 6H), 3.08 (s, 3H), 6.61 (dd, 1H), 6.75-6.80 (m, 1H), 7.93-7.96 (m, 1H); m/z 210 (M+H)+

Provenance & Evidence