반응 #517961

반응 방정식

hydrochloric acid

Borane-trimethylamine complex

hydrochloric acid

4-methoxyindole

→

desired compound

수율 83.0%

4-methoxyindoline

수율 83.0%

용매

dioxane

반응 조건

후처리

1. 1
   온도the mixture was heated
2. 2
   온도to reflux for 30 minutes
3. 3
   온도the mixture was heated
4. 4
   온도to reflux for 15 minutes
5. 5
   기타The solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution
6. 6
   workup.ADDITIONwas added
7. 7
   추출by extracting the aqueous layer with ether (3×20 ml)
8. 8
   세척The obtained organic layers were washed with saturated brine
9. 9
   건조dried over sodium sulfate
10. 10
    기타After removing solids
11. 11
    여과by filtration
12. 12
    기타the solvent was removed under reduced pressure
13. 13
    기타the obtained crude product
14. 14
    기타was purified by silica gel column chromatography

실험 절차

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%).

출처