Réaction #78329

Équation de réaction

2-(chloromethyl)-acrylonitrile

2-hydroxyethylphosphonic acid dimethylester

triethylamine

TEA

2-(chloromethyl)-acrylonitrile

→

colourless liquid

Rendement 54.2%

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

Rendement 54.2%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températureunder reflux
2. 2
   Températureis heated for a further 24 hours
3. 3
   Températureunder reflux
4. 4
   TempératureAfter the reaction mixture has cooled
5. 5
   Filtrationthe formed deposit of TEA hydrochloride is filtered out and
6. 6
   Lavageis washed twice with 50 ml THF
7. 7
   ConcentrationAfter the THF phases have been concentrated on the rotary evaporator
8. 8
   Lavagewashed twice with water
9. 9
   SéchageAfter it has been dried over anhydrous sodium sulphate
10. 10
    Concentrationthe mixture is concentrated
11. 11
    workup.DISTILLATIONdistillation in the fine vacuum

Mode opératoire

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).

Source