反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 0 °C
PROCEDURE
实验过程
A stirred solution of imidazo[4,5-c]pyridine (10.0 g. 0.084 mol) in dry dimethylformamide (100 ml) at 18° C. under a nitrogen atmosphere, was treated with sodium hydride (5.04 g of 60% dispersion in mineral oil, 0.126 mol) in portions over a period of 5 minutes. The mixture was stirred for an additional 2.5 hours until hydrogen evolution had ceased. The mixture was cooled to 0° C., treated with ethyl 4-bromomethylbenzoate (22.6 g, 0.093 mol), allowed to warm up to room temperature and then stirred for an additional 18 hours. The mixture was diluted with ethyl acetate (600 ml), washed with water (3×200 ml) and dried over anhydrous sodium sulphate. The solvent was evaporated off under reduced pressure to yield an impure mixture of isomers which was purified by chromatography (silica gel, chloroform) to yield a less polar isomer which was recrystallized from ethyl acetate-hexane to yield ethyl 4-(3H-imidazo[4,5-c]pyridin-3-ylmethyl)benzoate as a colorless crystalline solid, having a melting point of 110°-111.5° C. and the following physical characteristics:
WORKUP
后处理
- temperatureto warm up to room temperature
- washwashed with water (3×200 ml)
- dry with materialdried over anhydrous sodium sulphate
- customThe solvent was evaporated off under reduced pressure
- customto yield
- additionan impure mixture of isomers which
- customwas purified by chromatography (silica gel, chloroform)
- customto yield a less polar isomer which
- customwas recrystallized from ethyl acetate-hexane