تفاعل #77745

معادلة التفاعل

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

المردود 57.2%

المذيبات

EtOAc

water

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر