Methyl iodide → 1,4-Dimethoxy-1-(3-methylbutyl)naphthalen-2(1h)-one

Participants

Reaction Steps

To a solution of Example 11A (40 mg, 0.154 mmol) in N,N-dimethylformamide (1 mL) at 0° C. was added 60% wt sodium hydride (24.6 mg, 0.616 mmol). The reaction solution was stirred for 0.5 h and methyliodide (0.038 mL, 0.616 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 a white solid (35.4 mg, 84%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.55-0.65 (m, 1H), 0.68 (dd, J=6.80 Hz, 6H), 0.85-1.00 (m, 1H), 1.20-1.33 (m, 1H), 1.56-1.96 (m, 2H), 2.76-2.86 (s, 3H), 3.96-4.02 (s, 3H), 5.48-5.84 (s, 1H), 7.25-7.70 (m, 3H), 7.82 (d, J=7.72 Hz, 1H); MS m/z 274.9 (M+H)+.

Provenance & Evidence