Benzyl Bromide → 1-(Benzyloxy)-4-methoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

Participants

Reaction Steps

To a solution of Example 11A (25 mg, 0.094 mmol) in N,N-dimethylformamide (1 mL) at 0° C. was added 60% wt sodium hydride (15.4 mg, 0.384 mmol). The reaction solution was stirred for 0.5 h and benzylbromide (0.046 mL, 0.384 mmol) was added. The solution was stirred 16 h at room temperature, quenched with saturated NH4Cl, and extracted with ethyl acetate. The organic extract was concentrated in vacuo. Column chromatography on silica (20% ethyl acetate/hexane) afforded the title compound as an oil (29 mg, 86%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.71 (dd, 6H), 0.80-1.03 (m, 2H), 1.19-1.38 (m, 1H), 1.69-2.04 (m, 2H), 3.85 (d, J=10.66 Hz, 1H), 3.98 (s, 3H), 4.04 (d, J=11.03 Hz, 1H), 5.84 (s, 1H) 7.19-7.39 (m, 5H), 7.40-7.57 (m, 1H), 7.58-7.71 (m, 2H), 7.85 (d, J=7.72 Hz, 1H); MS m/z 351.1 (M+H)+.

Provenance & Evidence