Reaction #526777

Reaction equation

2-phenyl-4-formyl-5-methyl-1H-imidazole

2-chloropropane

magnesium

→

2-phenyl-4-(1-hydroxy-2-methylpropyl)-5-methyl-1H-imidazole

Yield 57.9%

Solvents

THF

diethyl ether

Conditions

Workup

1. 1
   workup.ADDITIONAt the end of the addition
2. 2
   Temperaturethe mixture was refluxed for 30 minutes
3. 3
   Temperaturecooled
4. 4
   workup.ADDITIONpoured on ice water
5. 5
   ExtractionThe aqueous layer was extracted twice with 100 ml of diethyl ether
6. 6
   OtherEvaporation of the solvent
7. 7
   Othergave a residue which
8. 8
   Otherwas recrystallized in ethanol

Procedure

35 Grams (0.45 mol) of 2-chloropropane was added to 10.8 g (0.45 mol) of magnesium in 100 ml of diethyl ether. Then 55.8 g (0.3 mol) of 2-phenyl-4-formyl-5-methyl-1H-imidazole in 100 ml of THF were added. At the end of the addition, the mixture was refluxed for 30 minutes and then cooled and poured on ice water. The aqueous layer was extracted twice with 100 ml of diethyl ether. Evaporation of the solvent gave a residue which was recrystallized in ethanol to yield 40 grams of 2-phenyl-4-(1-hydroxy-2-methylpropyl)-5-methyl-1H-imidazole, which melted at 214° C.

Source