반응 #409560

반응 방정식

water

Sodium hydride

1-[3-(4-hydroxyphenyl)propyl]imidazole

2-(4-benzyloxyphenyl)-4-chloromethyloxazole

→

2-(4-benzyloxyphenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

수율 62.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred for further 3 hours at 80° C
2. 2
   추출extracted with ethyl acetate
3. 3
   세척The ethyl acetate layer was washed with water
4. 4
   건조dried (MgSO4)
5. 5
   농축concentrated
6. 6
   기타A crystalline product obtained from the fraction
7. 7
   세척eluted with ethyl acetate-methanol (50:1, v.v)
8. 8
   기타was recrystallized from ethanol

실험 절차

Sodium hydride (440 mg) was added, at room temperature, to a solution of 1-[3-(4-hydroxyphenyl)propyl]imidazole (2.02 g) in N,N-dimethylformamide (50 ml). The mixture was stirred for 1.5 hour, to which was added 2-(4-benzyloxyphenyl)-4-chloromethyloxazole (3.60 g). The mixture was stirred for further 3 hours at 80° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated. The residue was subjected to a silica gel column chromatography. A crystalline product obtained from the fraction eluted with ethyl acetate-methanol (50:1, v.v) was recrystallized from ethanol to give 2-(4-benzyloxyphenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole (2.88 g, 62%) as colorless prisms, mp 133-134° C.

출처