反应详情

6-Bromo-1-indanone (142 g, 672 mmol) in tetrahydrofuran (1200 mL) was added slowly to refluxing dimethyl carbonate (143 mL, 1680 mmol), sodium hydride (80.6 g, 2020 mmol, 60% in oil, washed with pentane after weighing) and tetrahydrofuran (1200 mL). After refluxing the mixture for 2.5 hours, acetic acid (240 mL) was added dropwise at 0° C. and then allowed to warm to room temp. The mixture was partitioned between diethyl ether/dichloromethane and dilute aqueous hydrochloric acid. The organic layer was washed with 2N hydrochloric acid, water, aqueous sodium bicarbonate, and brine and was then dried over sodium sulfate to obtain a brown solid after removing solvent under vacuum, (176 g, 97%, crude), 124.5-127.5° C. m.p. 1H-NMR (300 MHz, CDCl3) (a ratio of approximately 3:1 enol to ketone tautomers) 7.91 (d, 0.27H), 7.77 (d, 0.73H, J=1.8), 7.73 (dd, 0.27H), 7.54 (dd, 0.73H, J=8.1, 1.8), 7.39 (d, 0.27H), 7.34 (d, 0.73H, J=7.9), 3.86 (s, 2.19H), 3.83 (m, 0.27H), 3.80 (s, 0.81H), 3.50 (m, 0.27H), 3.47 (s, 1.46H), 3.32 (m, 0.27H).

1. temperatureAfter refluxing the mixture for 2.5 hours
2. customThe mixture was partitioned between diethyl ether/dichloromethane and dilute aqueous hydrochloric acid
3. washThe organic layer was washed with 2N hydrochloric acid, water, aqueous sodium bicarbonate, and brine
4. dry with materialwas then dried over sodium sulfate
5. customto obtain a brown solid
6. customafter removing solvent under vacuum, (176 g, 97%, crude), 124.5-127.5° C.