Reaktion #63852

Reaktionsgleichung

sodium hydride

diethyl cyanomethylphosphonate

(E)-2-ethyl-2-butenal

→

(E,E)-4-ethyl-2,4-hexadienenitrile

Ausbeute 41.0%

Lösungsmittel

benzene

benzene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGAfter stirring for 60 minutes at room temperature
2. 2
   workup.STIRRINGat 0° C. with stirring
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   WaschenThe extract was washed successively with water and brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   SonstigeRemoval of the solvent
7. 7
   Sonstigegave an oil which
8. 8
   workup.DISTILLATIONwas purified by distillation under reduced pressure

Vorschrift

To a mixture of sodium hydride (60% in oil, 7.5 g) and dry benzene (200 ml) was added dropwise diethyl cyanomethylphosphonate (30 g) with stirring at 0° C. under dry nitrogen atmosphere. After stirring for 60 minutes at room temperature, a solution of (E)-2-ethyl-2-butenal (16.6 g) in dry benzene was added thereto at 0° C. with stirring. The resulting mixture was allowed to stand at room temperature for 60 minutes and diluted with water and then extracted with ethyl acetate. The extract was washed successively with water and brine, and then dried over magnesium sulfate. Removal of the solvent gave an oil which was purified by distillation under reduced pressure to give (E,E)-4-ethyl-2,4-hexadienenitrile (8.4 g).

Quelle