Reaktion #77745

Reaktionsgleichung

HCl

6-Hydroxy-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester

DMF

1,4-dibromobutene

→

6-(4-Bromo-but-2-enyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester

Ausbeute 57.2%

Lösungsmittel

EtOAc

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe inorganic phase was extracted with EtOAc
2. 2
   WaschenThe combined organic phases were washed with water
3. 3
   Trocknendried over Na2SO4
4. 4
   SonstigeThe crude product was purified by column chromatography on silica gel with hexane/EtOAc 9:1 to 4:1

Vorschrift

To 304 mg (1 mmol) 6-Hydroxy-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester in 4 ml DMF 420 mg (3 mmol) K2CO3 (powdered) and 416 mg (2 mmol) 1,4-dibromobutene were added. The mixture was stirred at 50° C. for 1 h, diluted with EtOAc and water. 2M HCl was added and the inorganic phase was extracted with EtOAc. The combined organic phases were washed with water and dried over Na2SO4. The crude product was purified by column chromatography on silica gel with hexane/EtOAc 9:1 to 4:1 to yield 250 mg (46%) 6-(4-Bromo-but-2-enyloxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid 4-chloro-phenyl ester as colorless gum, MS: 436 (MH+, 1Br, 1Cl).

Quelle