반응 #77771

반응 방정식

5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

K2CO3

1,4-dibromobutene

→

5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

수율 31.9%

용매

DMF

ether

water

반응 조건

후처리

1. 1
   온도cooled to RT
2. 2
   추출The aqueous phase was extracted with ether
3. 3
   세척the organic phases were washed with water
4. 4
   건조dried over Na2SO4

실험 절차

514 mg (2.3 mmol) 5-Hydroxy-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester in 12 ml DMF were treated with 830 mg (6 mmol) powdered K2CO3 and 1070 mg (5 mmol) 1,4-dibromobutene. The suspension was stirred at 50° C. for 3 h, cooled to RT, diluted with ether and water. The aqueous phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Column chromatography on silica gel with hexane/EtOAc 9:1 yielded 270 mg (31%) 5-(4-Bromo-but-2-enyloxy)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester as colorless solid, MS: 368 (MH+, 1Br).

출처