Reacción #81298

Ecuación de reacción

ammonium chloride

methylmagnesium iodide

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

diethyl ether

→

title compound

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling, to the mixture
2. 2
   OtroThe tetrahydofuran layer was separated
3. 3
   Lavadowashed with a saturated aqueous solution of sodium chloride
4. 4
   Concentraciónconcentrated by evaporation under reduced pressure
5. 5
   Otroto give a concentrate
6. 6
   ExtracciónThe aqueous layer was once again extracted with a small amount of ethyl acetate
7. 7
   LavadoThe extract was washed with a saturated aqueous solution of sodium chloride
8. 8
   Otrodried
9. 9
   Concentraciónconcentrated by evaporation under reduced pressure
10. 10
    ExtracciónThe resulting extract
11. 11
    Otrothe 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
    Otrothe product was crystallized from a mixture of ethyl acetate and hexane

Procedimiento

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).

Fuente