1,4-Dimethoxy-1-(3-methylbutyl)naphthalen-2(1h)-one → 4-Methoxy-4-(3-methylbutyl)naphthalene-1,3(2h,4h)-dione

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Reaction Steps

A solution of Example 11B (35 mg, 0.127 mmol) in methanol (0.25 mL) and 1 N NaOH (0.25 mL) was stirred at 40° C. for 6 hours. The solution was concentrated in vacuo. Column chromatography on silica (7% methanol/dichloromethane) afforded the title compound (30 mg, 90%). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.30-0.47 (m, 1H), 0.67 (dd, J=13.97, 6.62 Hz, 6H), 0.75-0.93 (m, 1H), 1.10-1.37 (m, 1H), 1.70-1.95 (m, 1H), 1.98-2.21 (m, 1H), 2.81 (s, 3H), 5.70-5.83 (m, 1H), 7.47 (t, 1H), 7.60 (d, 1H), 7.65 (t, 1H), 7.90 (d, J=7.72 Hz, 1H); MS (ESI) m/z 260.9 (M+H)+.

Provenance & Evidence