反应详情

To a solution of ethyl 8-(phenylselanyl)-1,4-dioxaspiro[4.5]decane-8-carboxylate (14.00 g, 38.00 mmol) in dichloromethane (100 mL) was added 30% hydrogen peroxide solution (11.6 mL, 380.0 mmol). The reaction mixture was stirred at ambient temperature for 16 h then diluted with dichloromethane (100 mL), washed with saturated sodium hydrogencarbonate (100 mL), saturated ammonium chloride (3×75 mL), and brine (3×75 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was purified by column chromatography with ethyl acetate in hexanes (10%) to afford the title compound as a colorless liquid (6.10 g, 76%): 1H NMR (300 MHz, CDCl3) δ 6.82 (m, 1H), 4.11 (dd, J=7.1 Hz, 2H), 3.92 (s, 4H), 2.49-2.43 (m, 2H), 2.34-2.29 (m, 2H), 1.76-1.65 (m, 4H), 1.21 (t, J=7.1 Hz, 3H).

1. washwashed with saturated sodium hydrogencarbonate (100 mL), saturated ammonium chloride (3×75 mL), and brine (3×75 mL)
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo to dryness
5. customThe residue was purified by column chromatography with ethyl acetate in hexanes (10%)