Water → [2-methoxy-1-(3-methylbutyl)-4-oxo-1,4-dihydronaphthalen-1-yl]methyl Acetate

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Reaction Steps

To a solution of Example 179B (0.15 g, 0.5 mmol) in benzene (5 mL) was added celite (0.15 g), pyridinium dichromate (0.75 g, 2.0 mmol), and a solution of 70% t-butyl peroxide in water (0.25 mL, 2.0 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 (5% to 15% ethyl acetate/hexane gradient) afforded the product as colorless oil (0.12 g, 75%). 1H NMR (300 MHz, CDCl3) δ ppm 0.53 (m, 1H), 0.76 (m, 7H), 1.35 (m, 1H), 1.73 (s, 3H), 1.80 (m, 1H), 2.09 (m, 1H), 3.84 (s, 3H), 4.51 (m, 2H), 5.97 (s, 1H), 7.43 (m, 2H), 7.59 (m, 1H), 8.20 (d, J=7.72 Hz, 1H); MS m/z 317.1 (M+H)+.

Provenance & Evidence