Reaktion #303399

Reaktionsgleichung

1,4-dibromobutane

Sodium hydride

(3-bromo-phenyl)-acetic acid ethyl ester

18-crown-6

→

1-(3-bromo-phenyl)-cyclopentanecarboxylic acid ethyl ester

Ausbeute 91.2%

Lösungsmittel

water

N,N′-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture is stirred for 18 hours at ambient temperature
2. 2
   Extraktionextracted thrice with EtOAc (60 mL)
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated

Vorschrift

Sodium hydride (60% in oil, 1.07 g, 26.8 mmol) is added to a solution of (3-bromo-phenyl)-acetic acid ethyl ester [2.59 g, 10.7 mmol] and 18-crown-6 (catalytic amount) in N,N′-dimethylformamide (50 mL). The mixture is stirred for 25 minutes and 1,4-dibromobutane (1.41 mL, 11.8 mmol) is added dropwise via syringe. The mixture is stirred for 18 hours at ambient temperature, diluted with water (100 mL) and extracted thrice with EtOAc (60 mL). The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated to afford 1-(3-bromo-phenyl)-cyclopentanecarboxylic acid ethyl ester [2.9 g, 91%] as an oil, which is used without further purification.

Quelle