Reaktion #6037

Reaktionsgleichung

potassium tert-butoxide

ethylene glycol dimethyl ether

4-acetylbenzonitrile

p-toluenesulfonylmethylisocyanide

→

2-(4-cyanophenyl)ethylcyanide

Ausbeute 70.4%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.WAITat 40° C. for an additional hour
3. 3
   TemperaturAfter the reaction mixture was cooled
4. 4
   Sonstigeto stand at room temperature
5. 5
   Filtrationit was filtered under reduced pressure
6. 6
   Sonstigethe filtrate was purified by silica gel chromatography

Vorschrift

1.40 g (1.25 mmole) of potassium tert-butoxide was added to a 17 ml ethylene glycol dimethyl ether solution containing 0.73 g (5 mmole) of 4-acetylbenzonitrile, 0.5 ml of ethanol and 1.27 g (6.5 mmole) of p-toluenesulfonylmethylisocyanide under ice-cooling; then the mixture was stirred at room temperature for 0.5 hour and then at 40° C. for an additional hour. After the reaction mixture was cooled by allowing to stand at room temperature, it was filtered under reduced pressure and the filtrate was purified by silica gel chromatography to obtain 0.55 g (yield: 70.4 %) of 2-(4-cyanophenyl)ethylcyanide.

Quelle