反应详情

Borane-trimethylamine complex (3.00 g) and 10.5N hydrochloric acid (2.25 ml) were added to 4-methoxyindole (1.29 g) in dioxane (20 ml), and the mixture was heated to reflux for 30 minutes. To this mixture, 6N hydrochloric acid (7.00 ml) was added and the mixture was heated to reflux for 15 minutes. The solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution was added to change the aqueous layer to alkaline condition, followed by extracting the aqueous layer with ether (3×20 ml). The obtained organic layers were washed with saturated brine and dried over sodium sulfate. After removing solids by filtration, the solvent was removed under reduced pressure, and the obtained crude product was purified by silica gel column chromatography to obtain the desired compound (1.08 g, yield: 83%).

1. temperaturethe mixture was heated
2. temperatureto reflux for 30 minutes
3. temperaturethe mixture was heated
4. temperatureto reflux for 15 minutes
5. customThe solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution
6. additionwas added
7. extractionby extracting the aqueous layer with ether (3×20 ml)
8. washThe obtained organic layers were washed with saturated brine
9. dry with materialdried over sodium sulfate
10. customAfter removing solids
11. filtrationby filtration
12. customthe solvent was removed under reduced pressure
13. customthe obtained crude product
14. customwas purified by silica gel column chromatography