Reaction #831221

Reaction equation

4-(1-(triphenylmethyl)imidazol-4-yl)butanenitrile

3-phenylpropylmagnesium bromide

diethyl ether

ammonium chloride

→

1-(1H-Imidazol-4-yl)-7-phenylheptan-4-one

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Temperatureto reflux for 6 h
2. 2
   OtherHydrolysis
3. 3
   Otherthe organic phase is separated
4. 4
   Otherfor 2 h
5. 5
   OtherThe ethanol is removed under vacuum, filtration
6. 6
   workup.STIRRINGThe title compound is stirred in dichloromethane
7. 7
   Otherrecrystallized in the hydrogenmaleate form from ethanol/diethyl ether

Procedure

5 mmol of 4-(1-(triphenylmethyl)imidazol-4-yl)butanenitrile are introduced into a solution of 3-phenylpropylmagnesium bromide in 300 ml of diethyl ether and 100 ml of tetrahydrofuran and the mixture is brought to reflux for 6 h. Hydrolysis is carried out with an ammonium chloride solution, the organic phase is separated and the aqueous phase is stirred with dichloromethane. The combined and concentrated organic phases are brought to boiling point for 2 h in a 2N aqueous/alcohol (ethanol/water) hydrochloric acid solution. The ethanol is removed under vacuum, filtration is carried out and basification is carried out. The title compound is stirred in dichloromethane and recrystallized in the hydrogenmaleate form from ethanol/diethyl ether.

Source