Reacción #65251

Ecuación de reacción

tetrahydrofuran

2-n-butyl-1-(2-chlorophenyl)methyl-1H- imidazol-carboxaldehyde

methyl lithium

→

2-n-butyl-1-(2-chlorophenyl)methyl-5-(a-hydroxy) ethyl-1H-imidazole

Rendimiento 92.0%

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched with ammonium chloride solution
2. 2
   Temperaturawarmed to ambient temperature
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   OtroThe washed, dried
5. 5
   Otroconcentrated product was flashed chromatographed over silica gel with ethyl acetate

Procedimiento

A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H- imidazol-carboxaldehyde (Example 1 (iii)) (1.1 g, 3.97 mmol) was dissolved in dry tetrahydrofuran (15 mL), cooled to -78° C. under argon and a solution of methyl lithium (3.64 ml of 1.2M in diethyl ether, 4.57 mmol) was added dropwise. The mixture was stirred for 1.5 hours, quenched with ammonium chloride solution, warmed to ambient temperature and extracted with ethyl acetate. The washed, dried, concentrated product was flashed chromatographed over silica gel with ethyl acetate to provide 1.07 g (92%) of 2-n-butyl-1-(2-chlorophenyl)methyl-5-(a-hydroxy) ethyl-1H-imidazole.

Fuente