Reaction #65251

Reaction equation

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

Yield 92.0%

Conditions

Workup

1. 1
   Otherquenched with ammonium chloride solution
2. 2
   Temperaturewarmed to ambient temperature
3. 3
   Extractionextracted with ethyl acetate
4. 4
   OtherThe washed, dried
5. 5
   Otherconcentrated product was flashed chromatographed over silica gel with ethyl acetate

Procedure

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