Research On The Etherification Of Ester Of Pyrrole-2-Methanol Compound

Pyrrole compounds have received a great deal of attention, due to their importance in organic chemistry and pharmaceutical chemistry. In the course of study on the synthesis of pyrrole compounds pocessing potential bioactivity, we found two novel types of etherification of 2-acyloxymethylpyrrole compounds with alcohols catalyzed by p-toluenesulfonic acid and with sodium alkoxide in corresponding alcohol, which have the advantages of mild reaction condition, high yields, labile work-up, and broad application scope. Therefore, our results will contribute to broadening the knowledge of pyrrole chemistry, offering an alternate preparation method of ether. In this thesis, the optimization of reaction conditions, application scope and mechanism of etherification of acetic acid pyrrol-2-ylmethyl ester compound will be described. It contains three chapters as belows:In chapter one, the preparation of ethers were reviewed.In chapter two, the etherification of 2-acyloxymethylpyrrole compounds with alcohols in the presence of p-toluene sulfonic acid as catalyst was described in detail. We firstly optimized the reaction conditions and studied its application scope. We found substituent on the N atom of the pyrrole ring has no effect on the etherification and tert-alcohols are not suitable for this reaction. Then, we proposed a reasonable mechanism to interpret the etherification based on the experimental results.In chapter three, the etherification of 2-acyloxymethylpyrrole compounds with sodium alkoxide using the corresponding alcohol as solvent was described in detail. We firstly optimized the reaction conditions and studied its application scope. We found substituent on the N of the pyrrole ring palyed an importment role and likewise, sodium tert-alkoxide and sodium salt of diols are not suitable. Then, we also proposed a possible mechanism.