반응 #40739

반응 방정식

sodium hydride

2-naphthalen-1-yl-1H-imidazole

iodoethane

→

title compound

1-ethyl-2-naphthalen-1-yl-1H-imidazole

용매

DMF

DMF

반응 조건

후처리

1. 1
   온도cooled to 0° C.
2. 2
   workup.STIRRINGThe mixture is stirred at rt for 1 hr
3. 3
   온도heated to 50° C.
4. 4
   workup.STIRRINGstirred for an additional 8 hr
5. 5
   온도The reaction mixture is cooled to rt
6. 6
   추출The mixture is extracted with EtOAc (100 ml×3)
7. 7
   세척The combined organic layers are washed with water and brine
8. 8
   건조dried over anhydrous sodium sulfate, and solvent
9. 9
   기타is evaporated at reduced pressure
10. 10
    기타The crude product is purified by flash chromatography on silica gel

실험 절차

To a suspension of sodium hydride (2.40 g, 60% mineral oil suspension, 60 mmol) in anhydrous DMF (30 ml) is added a solution of 2-naphthalen-1-yl-1H-imidazole (9.70 g, 50 mmol) in DMF (70 ml) at rt. The resulting mixture is stirred at 50° C. for 1 hr, and then cooled to 0° C., after which iodoethane (8.19 g, 52.5 mmol, 1.05 eq.) is added dropwise. The mixture is stirred at rt for 1 hr, and then heated to 50° C. and stirred for an additional 8 hr. The reaction mixture is cooled to rt, and poured into ice-water (500 ml). The mixture is extracted with EtOAc (100 ml×3). The combined organic layers are washed with water and brine, dried over anhydrous sodium sulfate, and solvent is evaporated at reduced pressure. The crude product is purified by flash chromatography on silica gel to give the title compound. LCMS 223 (M+1).

출처