Reaktion #77749

Reaktionsgleichung

6-Hydroxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

acetone

1,4-dibromobutane

→

6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester

Ausbeute 63.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Einengenthe filtrate was concentrated in vacuo
3. 3
   workup.ADDITIONEtOAc and water were added
4. 4
   Extraktionthe inorganic phase was extracted with EtOAc
5. 5
   Waschenthe combined organic phases were washed with water
6. 6
   Trocknendried over Na2SO4
7. 7
   SonstigeThe crude product was purified by column chromatography on silica gel with hexane/EtOAc 9:1

Vorschrift

To 11.6 g (46.5 mmol) 6-Hydroxy-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester in 200 ml acetone 18.6 g (134.8 mmol) K2CO3 (powdered) and 13.7 g (115.7 mmol) 1,4-dibromobutane were added. The mixture was stirred at reflux for 4 h and at RT over night. The reaction mixture was filtered, and the filtrate was concentrated in vacuo. EtOAc and water were added, the inorganic phase was extracted with EtOAc and 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 yield 11.1 g (63%) 6-(4-Bromo-butoxy)-3,4-dihydro-2H-quinoline-1-carboxylic acid tert-butyl ester as colorless oil, MS: 383 (M, 1Br).

Quelle