反应详情

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)+.

1. filtrationThe heterogenous solution was filtered through celite
2. additionThe filtrate was diluted with ethyl acetate (10 mL)
3. washwashed with 5% Na2S2O5 (10 mL)
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated in vacuo