Water → 3-Methoxy-4-(3-methylbutyl)-4-vinylnaphthalen-1(4h)-one

Participants

Reaction Steps

To a solution of Example 181B (0.13 g, 0.5 mmol) in benzene (5 mL) was added celite (0.13 g), pyridinium dichromate (0.38 g, 1.0 mmol), and a solution of 70% t-butyl peroxide in water (0.13 mL, 1.0 mmol). The heterogenous solution was filtered through celite. The filtrate was diluted with ethyl acetate (10 mL), washed with 5% Na2S2O5 (10 mL), dried (Na2SO4), and concentrated in vacuo. Column Chromatography on silica (20% dichloromethane/hexane -15% ethyl acetate/hexane) afforded product as a light yellow oil (46 mg, 35%). 1H NMR (300 MHz, CDCl3) δ ppm 0.51 (m, 1H), 0.76 (m, 7H), 1.37 (m, 1 H), 2.01 (m, 1H), 2.33 (m, 1H), 3.81 (s, 3H), 5.12 (m, 2H), 5.94 (m, 2H), 7.37 (m, 2H), 7.54 (m, 1H), 8.18 (d, J=8.09 Hz, 1H); MS m/z 270.9 (M+H)+.

Provenance & Evidence