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.

Key words: 2-acetoxymethylpyrrole derivative, 2-alkoxymethylpyrrole derivative, etherification, azafulvene, alcohol