反应详情

Sodium hydride (60% in mineral oil, 0.524 g, 13.1 mmol) was added to a solution of C7 (3.20 g, 10.9 mmol) in tetrahydrofuran (20 mL), and the reaction mixture was heated at reflux for 1.5 hours, then allowed to sit at room temperature for 90 hours. Additional sodium hydride (1 equivalent) was added, and the reaction mixture was heated at reflux for 3 hours. After cooling to room temperature, the mixture was quenched with water, diluted with saturated aqueous sodium chloride solution, and extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane) afforded the product as a solid. Yield: 1.51 g, 7.12 mmol, 65%. 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.38 (s, 1H), 8.03 (s, 1H), 4.19 (s, 3H).

1. temperaturethe reaction mixture was heated
2. temperatureat reflux for 1.5 hours
3. temperaturethe reaction mixture was heated
4. temperatureat reflux for 3 hours
5. customthe mixture was quenched with water
6. additiondiluted with saturated aqueous sodium chloride solution
7. extractionextracted with ethyl acetate
8. dry with materialThe combined organic layers were dried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customPurification via silica gel chromatography (Gradient: 0% to 100% ethyl acetate in heptane)