Reaction #54820

Reaction equation

Bromomethyl 2-naphthoyl ketone dimethyl ketal

Sodium hydroxide

imidazole

hydrogen

→

1-[2-(2-naphthyl)-2,2-dimethoxyethyl]imidazole

Solvents

dimethylformamide

water

dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted with ether (400 ml total)
2. 2
   Washthe extracts washed
3. 3
   Dryingdried (MgSO4)
4. 4
   Otherevaporated
5. 5
   OtherThe resulting crude solid (2.2 g) is recrystallized from toluene

Procedure

Sodium hydroxide (0.40 g. of 50% dispersion in mineral oil) is added to 0.61 g. imidazole in 10 ml dimethylformamide and the mixture stirred at room temperature until the evolution of hydrogen is complete. Bromomethyl 2-naphthoyl ketone dimethyl ketal (2.21 g.) in 5 ml. dimethylformamide is then added and the mixture stirred for 24 hours at 110° under nitrogen. The resulting solution is poured into water (400 ml), extracted with ether (400 ml total), and the extracts washed, dried (MgSO4) and evaporated. The resulting crude solid (2.2 g) is recrystallized from toluene to give 1-[2-(2-naphthyl)-2,2-dimethoxyethyl]imidazole as a colorless solid.

Source