반응 #81298

반응 방정식

ammonium chloride

methylmagnesium iodide

2-butyl-1-tritylimidazole-4,5-dicarbonitrile

diethyl ether

→

title compound

4-Acetyl-2-butyl-5-cyano-1-tritylimidazole

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도cooling, to the mixture
2. 2
   기타The tetrahydofuran layer was separated
3. 3
   세척washed with a saturated aqueous solution of sodium chloride
4. 4
   농축concentrated by evaporation under reduced pressure
5. 5
   기타to give a concentrate
6. 6
   추출The aqueous layer was once again extracted with a small amount of ethyl acetate
7. 7
   세척The extract was washed with a saturated aqueous solution of sodium chloride
8. 8
   기타dried
9. 9
   농축concentrated by evaporation under reduced pressure
10. 10
    추출The resulting extract
11. 11
    기타the resulting crude product was purified by column chromatography through silica gel
12. 12
    workup.ADDITIONby volume mixture of hexane and ethyl acetate as the eluent
13. 13
    기타the product was crystallized from a mixture of ethyl acetate and hexane

실험 절차

11.1 ml of a 2M solution of methylmagnesium iodide in diethyl ether was slowly added dropwise at room temperature, in an atmosphere of nitrogen, to a solution of 4.5 g of 2-butyl-1-tritylimidazole-4,5-dicarbonitrile [prepared as described in step (i) above] in 45 ml of tetrahydrofuran, and the resulting mixture was stirred at room temperature for 3 hours. At the end of this time, a saturated aqueous solution of ammonium chloride was added dropwise, whilst ice-cooling, to the mixture. The tetrahydofuran layer was separated, washed with a saturated aqueous solution of sodium chloride and concentrated by evaporation under reduced pressure to give a concentrate. The aqueous layer was once again extracted with a small amount of ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried and concentrated by evaporation under reduced pressure. The resulting extract was combined with the above concentrate, and the resulting crude product was purified by column chromatography through silica gel, using a 3:1 by volume mixture of hexane and ethyl acetate as the eluent, and the product was crystallized from a mixture of ethyl acetate and hexane, to give 1.46 g of the title compound, melting at 159°-160° C. (with decomposition).

출처