对甲苯磺酸催化的2-乙酰氧甲基吡咯衍生物和醇的醚化反应研究

Etherification of 2-Acetoxymethylpyrrole Derivative with Alcohol Catalyzed by para-Toluenesulfonic Acid

研究了对甲苯磺酸催化的2-乙酰氧甲基吡咯衍生物和醇之间的醚化反应,结果以优秀的收率生成了相应的2-烷氧甲基吡咯衍生物.该反应具有条件温和、产物得率高和后处理简单等优点,提供了一种在弱酸条件下制备2-烷氧甲基吡咯衍生物的新方法,提出了一种基于氮杂富勒烯过渡态的反应机理用于解释实验现象.

Etherification of 2-acetoxymethylpyrrole derivatives with alcohols catalyzed by para-toluenesulfonic acid was investigated in details resulting in the smooth formation of the corresponding 2-alkoxymethylpyrrole derivatives in excellent yields. An alternate method for the preparation of 2-alkoxymethylpyrrole derivatives starting from 2-acetoxymethylpyrrole derivatives under weak acidic condition was provided. The main advantages of the developed methodology are mild reaction conditions, high yields of products and simple work-up procedure. A plausible mechanism involving the generation of highly reactive azafulvene intermediate 4 was proposed to explain the observed phenomena.