反応 #347920

反応方程式

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

収率 92.0%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他quenched with ammonium chloride solution
2. 2
   温度warmed to ambient temperature
3. 3
   抽出extracted with ethyl acetate
4. 4
   その他The washed, dried
5. 5
   その他chromatographed over silica gel with ethyl acetate

実験手順

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.

出典