反应详情

To a solution of N-tert-butyl-1H-indole-6-sulfonamide (3.60 g, 14.2 mmol) and cyclohexanone (4.50 ml, 43.4 mmol) in methanol (72 ml) was added 28% sodium methoxide in methanol solution (17 ml), and the mixture was stirred for 12 hr with heating under reflux. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. 2N Hydrochloric acid was added to the residue, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1) to give N-tert-butyl-3-(cyclohex-1-enyl)-1H-indole-6-sulfonamide (2.82 g, yield 59.7%).

1. temperaturewith heating
2. temperatureunder reflux
3. concentrationconcentrated under reduced pressure
4. addition2N Hydrochloric acid was added to the residue
5. extractionthe mixture was extracted with ethyl acetate
6. washThe organic layer was washed with saturated brine
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationAfter filtration
9. customthe solvent was evaporated under reduced pressure
10. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=3:1-2:1)