تفاعل #517961

معادلة التفاعل

hydrochloric acid

Borane-trimethylamine complex

hydrochloric acid

4-methoxyindole

→

desired compound

المردود 83.0%

4-methoxyindoline

المردود 83.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was heated
2. 2
   درجة الحرارةto reflux for 30 minutes
3. 3
   درجة الحرارةthe mixture was heated
4. 4
   درجة الحرارةto reflux for 15 minutes
5. 5
   أخرىThe solvent was removed under reduced pressure and 1N aqueous sodium hydroxide solution
6. 6
   workup.ADDITIONwas added
7. 7
   استخلاصby extracting the aqueous layer with ether (3×20 ml)
8. 8
   غسيلThe obtained organic layers were washed with saturated brine
9. 9
   تجفيفdried over sodium sulfate
10. 10
    أخرىAfter removing solids
11. 11
    ترشيحby filtration
12. 12
    أخرىthe solvent was removed under reduced pressure
13. 13
    أخرىthe obtained crude product
14. 14
    أخرىwas purified by silica gel column chromatography

الإجراء التجريبي

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%).

المصدر