반응 #2355337

반응 방정식

6-Chloroindole

potassium carbonate

dimethyl carbonate

N,N-dimethylformamide

→

5-chloro-1-methylindole

수율 96.1%

반응 조건

후처리

1. 1
   온도heated
2. 2
   기타The starting indole was consumed within 3.5 h (as determined by HPLC)
3. 3
   온도After the mixture was then cooled to ˜3° C.
4. 4
   workup.ADDITIONice cold water (50 mL) was added
5. 5
   추출the resulting oily suspension was extracted with tert-butyl methyl ether (40 mL)
6. 6
   세척The separated organic layer was washed with water (3×25 mL)
7. 7
   기타was evaporated under vacuum

실험 절차

6-Chloroindole (1.0 g, 6.59 mmol), potassium carbonate (0.5 g), N,N-dimethylformamide (10 mL) and dimethyl carbonate (1.7 mL, 20.21 mmol) were stirred and heated to reflux (˜130° C.). The starting indole was consumed within 3.5 h (as determined by HPLC). After the mixture was then cooled to ˜3° C., ice cold water (50 mL) was added and the resulting oily suspension was extracted with tert-butyl methyl ether (40 mL). The separated organic layer was washed with water (3×25 mL), then was evaporated under vacuum to furnish 5-chloro-1-methylindole as a light yellow oil (1.05 g, 96.1% yield).

출처