Реакция #77745

Уравнение реакции

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

Выход 57.2%

Растворители

EtOAc

water

Условия реакции

Обработка

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

Методика

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).

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