تفاعل #303399

معادلة التفاعل

1,4-dibromobutane

Sodium hydride

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

18-crown-6

→

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

المردود 91.2%

المذيبات

water

N,N′-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture is stirred for 18 hours at ambient temperature
2. 2
   استخلاصextracted thrice with EtOAc (60 mL)
3. 3
   تجفيفdried over magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated

الإجراء التجريبي

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.

المصدر