反应详情

To a solution of 2,2,9-trimethyl-2H-pyrano[2,3-g]quinoline (4.36 g, 19.3 mmol) in chloroform (43.6 mL), a solution of m-chloroperbenzoic acid (7.35 g, 42.6 mmol) in chloroform (17.4 mL)-methanol (4.36 mL) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for 1 hour. Upon the completion of the reaction, the reaction solution was extracted with aqueous sodium thiosulfate solution and the resulting organic phase was washed with aqueous sodium hydrogencarbonate solution and then with aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, acetonitrile (19.3 mL), trimethylsilylcyanide (7.27 mL, 57.9 mmol) and triethylamine (5.38 mL, 38.6 mmol) were added to the residue at room temperature, and the resulting solution was stirred at 70° C. for 3.5 hours. Upon the completion of the reaction, aqueous sodium hydrogencarbonate solution was added to the reaction solution, and it was extracted with chloroform and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=2/1) and the aimed product was obtained (yield: 55%).

1. customUpon the completion of the reaction
2. extractionthe reaction solution was extracted with aqueous sodium thiosulfate solution
3. washthe resulting organic phase was washed with aqueous sodium hydrogencarbonate solution
4. dry with materialwith aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
5. additionwere added to the residue at room temperature
6. stirringthe resulting solution was stirred at 70° C. for 3.5 hours
7. additionwas added to the reaction solution, and it
8. extractionwas extracted with chloroform
9. dry with materialdried over anhydrous magnesium sulfate
10. distillationAfter distilling off the solvent
11. customthe residue was purified by column chromatography (hexane/ethyl acetate=2/1)