Reaction #2314280

Reaction equation

water

tosylate

potassium cyanide

→

(4-(4-Methyl-3-pentenyl)-3-cyclohexenyl)acetonitrile

Solvents

dimethylsulfoxide

Conditions

Workup

1. 1
   TemperatureThe reaction mixture is cooled to room temperature
2. 2
   Extractionextracted with hexane
3. 3
   DryingThe combined organic layers are dried over magnesium sulfate
4. 4
   Concentrationthe solution is concentrated in vacuo

Procedure

To a solution of tosylate 1H (R=4-Methyl-3-pentenyl) (20 g) in dimethylsulfoxide (178 mL) is added potassium cyanide (19.4 g). The reaction mixture is heated to 100° C., and the reaction mixture is stirred at that temperature for three hours. The reaction mixture is cooled to room temperature, added to water (300 mL), and extracted with hexane. The combined organic layers are dried over magnesium sulfate and the solution is concentrated in vacuo.

Source