反応 #78336

反応方程式

sodium hydride

ethyl 4-bromobutanoate

3,4-dichlorophenylaceto-nitrile

→

expected product

収率 45.8%

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

収率 45.8%

溶媒

THF

THF

THF

反応条件

後処理

1. 1
   温度cooled in an ice bath
2. 2
   温度It is cooled again in an ice bath
3. 3
   workup.STIRRINGthe mixture is stirred overnight at RT
4. 4
   濃縮It is concentrated under vacuum
5. 5
   抽出extracted with ether
6. 6
   洗浄the organic phase is washed with water, with a buffer solution of pH 2, with water and with saturated NaCl solution
7. 7
   乾燥dried over MgSO4
8. 8
   その他the solvent is evaporated off under vacuum
9. 9
   その他The residue is chromatographed on silica

実験手順

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.

出典