Reaktion #347920

Reaktionsgleichung

2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazole-5-carboxaldehyde

methyl lithium

→

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

Ausbeute 92.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with ammonium chloride solution
2. 2
   Temperaturwarmed to ambient temperature
3. 3
   Extraktionextracted with ethyl acetate
4. 4
   SonstigeThe washed, dried
5. 5
   Sonstigechromatographed over silica gel with ethyl acetate

Vorschrift

A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazole-5-carboxaldehyde (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 flash 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.

Quelle