Reacción #303494

Ecuación de reacción

ammonium chloride

Ethylmagnesium bromide

4-iodo-2-methyl-1-trityl-1H-imidazole

N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropanecarboxamide

→

(2-methyl-1-trityl-1H-imidazol-4-yl)[1-(trifluoromethyl)cyclopropyl]methanone

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato warm to ca. 12° C.
2. 2
   workup.STIRRINGAfter stirring at ambient temperature overnight
3. 3
   LavadoThe organic phase was washed with saturated aqueous sodium bicarbonate
4. 4
   Secadodried (magnesium sulfate)
5. 5
   Concentraciónconcentrated in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in a minimal volume of ether
7. 7
   workup.STIRRINGAfter stirring in heptane (ca. 3 L) for 1 h
8. 8
   Filtraciónsolid was collected by filtration
9. 9
   Lavadowashing with heptane

Procedimiento

Ethylmagnesium bromide (3 M solution in diethyl ether) (633 mL, 1.9 mol) was added over 1 h to a 5° C. solution of 4-iodo-2-methyl-1-trityl-1H-imidazole (855 g, 1.9 mol) in methylene chloride (8 L). After stirring at 5° C. for 30 min, the reaction mixture was allowed to warm to ca. 12° C. and a solution of N-methoxy-N-methyl-1-(trifluoromethyl)cyclopropanecarboxamide (355 g, 1.8 mol) in methylene chloride (2 L) was added over 1 h. After stirring at ambient temperature overnight, the reaction mixture was poured into saturated aqueous ammonium chloride. The organic phase was washed with saturated aqueous sodium bicarbonate, dried (magnesium sulfate) and concentrated in vacuo. The residue was dissolved in a minimal volume of ether and crashed out with heptane. After stirring in heptane (ca. 3 L) for 1 h, solid was collected by filtration, washing with heptane to afford (2-methyl-1-trityl-1H-imidazol-4-yl)[1-(trifluoromethyl)cyclopropyl]methanone.

Fuente