Reaktion #77771

Reaktionsgleichung

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

Ausbeute 31.9%

Lösungsmittel

DMF

ether

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled to RT
2. 2
   ExtraktionThe aqueous phase was extracted with ether
3. 3
   Waschenthe organic phases were washed with water
4. 4
   Trocknendried over Na2SO4

Vorschrift

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).

Quelle