反应详情

温度

90 °C

A mixture of ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0^[2,7]]trideca-1(9),2(7),3,5-tetraen-12-yl]acetate (3.00 g, 10.26 mmol, 1.00 equiv) and DDQ (5.83 g, 25.68 mmol, 2.50 equiv) in 1,4-dioxane (30 mL) was stirred for 2 h at 90° C. in an oil bath under nitrogen. The reaction mixture was cooled to room temperature and quenched with saturated aqueous Na2CO3, extracted with 3×40 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1) to provide the desired ethyl 2-[3-hydroxy-8-thia-4,6-diazatricyclo[7.4.0.0^[2,7]]trideca-1(9),2(7),3,5,10,12-hexaen-12-yl]acetate (2.00 g, 68%) as a yellow solid. LCMS (ES, m/z): 289 (M+H+).

1. temperatureThe reaction mixture was cooled to room temperature
2. customquenched with saturated aqueous Na2CO3
3. extractionextracted with 3×40 mL of ethyl acetate
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum
7. customThe residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:1)