Réaction #65251

Équation de réaction

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

Rendement 92.0%

Conditions de réaction

Traitement

1. 1
   Autrequenched with ammonium chloride solution
2. 2
   Températurewarmed to ambient temperature
3. 3
   Extractionextracted with ethyl acetate
4. 4
   AutreThe washed, dried
5. 5
   Autreconcentrated product was flashed chromatographed over silica gel with ethyl acetate

Mode opératoire

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.

Source