Imidazole → 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole

Participants

Reaction Steps

To a solution of imidazole (70 mg) in N,N-dimethylformamide (5 ml) was added, at 0° C., sodium hydride (60%, in oil, 50 mg). The mixture was stirred for one hour. To the reaction mixture was added 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethoxy]phenyl]propyl methanesulfonate (350 mg). The mixture was stirred for 1.5 hour at 70° C. The reaction mixture was diluted with water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The resulting crystalline product was recrystallized from ethyl acetate-hexane to give 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-[(E)-2-phenylethenyl]oxazole (200 mg, 61%) as colorless prisms, mp 127-128° C.

Provenance & Evidence