تفاعل #78336

معادلة التفاعل

sodium hydride

ethyl 4-bromobutanoate

3,4-dichlorophenylaceto-nitrile

→

expected product

المردود 45.8%

Ethyl 5-cyano-5-(3,4-dichlorophenyl)pentanoate

المردود 45.8%

المذيبات

THF

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled in an ice bath
2. 2
   درجة الحرارةIt is cooled again in an ice bath
3. 3
   workup.STIRRINGthe mixture is stirred overnight at RT
4. 4
   تركيزIt is concentrated under vacuum
5. 5
   استخلاصextracted with ether
6. 6
   غسيلthe organic phase is washed with water, with a buffer solution of pH 2, with water and with saturated NaCl solution
7. 7
   تجفيفdried over MgSO4
8. 8
   أخرىthe solvent is evaporated off under vacuum
9. 9
   أخرىThe residue is chromatographed on silica

الإجراء التجريبي

11.8 g of a 55% dispersion of sodium hydride in oil are suspended in 100 ml of THF and cooled in an ice bath, a solution of 50 g of 3,4-dichlorophenylaceto-nitrile in 50 ml of THF is added dropwise and the reaction mixture is stirred for 3 hours at RT. It is cooled again in an ice bath, a solution of 52.4 g of ethyl 4-bromobutanoate in 50 ml of THF is added dropwise and the mixture is stirred overnight at RT. It is concentrated under vacuum, the residue is taken up with water and extracted with ether, the organic phase is washed with water, with a buffer solution of pH 2, with water and with saturated NaCl solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using toluene and then a toluene/AcOEt mixture (100/5; v/v) as the eluent to give 36.9 g of the expected product.

المصدر