반응 #78329

반응 방정식

2-(chloromethyl)-acrylonitrile

2-hydroxyethylphosphonic acid dimethylester

triethylamine

TEA

2-(chloromethyl)-acrylonitrile

→

colourless liquid

수율 54.2%

2-[4-(dimethoxyphosphoryl)-2-oxabutyl]-acrylonitrile

수율 54.2%

용매

THF

반응 조건

후처리

1. 1
   온도under reflux
2. 2
   온도is heated for a further 24 hours
3. 3
   온도under reflux
4. 4
   온도After the reaction mixture has cooled
5. 5
   여과the formed deposit of TEA hydrochloride is filtered out and
6. 6
   세척is washed twice with 50 ml THF
7. 7
   농축After the THF phases have been concentrated on the rotary evaporator
8. 8
   세척washed twice with water
9. 9
   건조After it has been dried over anhydrous sodium sulphate
10. 10
    농축the mixture is concentrated
11. 11
    workup.DISTILLATIONdistillation in the fine vacuum

실험 절차

86.3 g (850 mmol) 2-(chloromethyl)-acrylonitrile are added dropwise at room temperature to a solution of 130.9 g (850 mmol) 2-hydroxyethylphosphonic acid dimethylester, 85.9 g (850 mmol) triethylamine (TEA) and 40 mg phenothiazine (stabilizer) in 1 l THF. Subsequently, the mixture is heated for 6 hours at 65° C. under reflux. 9.1 g (90 mmol) TEA and 9.1 g (90 mmol) 2-(chloromethyl)-acrylonitrile are once again added one after the other and the mixture is heated for a further 24 hours under reflux. After the reaction mixture has cooled, the formed deposit of TEA hydrochloride is filtered out and is washed twice with 50 ml THF. After the THF phases have been concentrated on the rotary evaporator, the residual raw product is taken up in 650 ml methylene chloride and washed twice with water. After it has been dried over anhydrous sodium sulphate, the mixture is concentrated and the residual liquid undergoes fractional distillation in the fine vacuum. 101.0 g (54% yield) of a colourless liquid results at b.p. 150° C. (0.05 mbar).

출처