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

Participants

Reaction Steps

To a solution of Example 180A (39 mg, 0.11 mmol) in benzene (1 mL) was added celite (39 mg), pyridinium dichromate (0.17 g, 0.45 mmol), and a solution of 70% t-butyl peroxide in water (58 μL, 0.45 mmol). The heterogenous solution was filtered through celite. The filtrate was diluted with ethyl acetate (3 mL), washed with 5% Na2S2O5 (3 mL), dried (Na2SO4), and concentrated in vacuo. Column chromatography on silica (10%-20% ethyl acetate/hexane) afforded product as a white solid (33 mg, 83%). 1H NMR (300 MHz, CDCl3) δ ppm 0.53 (m, 1H), 0.75 (m, 7H), 0.93 (d, J=5.88 Hz, 3H), 1.03 (d, J=5.88 Hz, 3H), 1.34 (m, 1H), 1.79 (m, 1H), 2.08 (m, 1H), 3.84 (s, 3H), 4.13 (m, 1H), 4.41 (d, J=10.30 Hz, 2H), 4.57 (m, 1H), 5.96 (s, 1H), 7.43 (m, 2H), 7.59 (m, 1H), 8.19 (d, J=7.72 Hz, 1H).

Provenance & Evidence