Convenient decagram scale preparation of ethyl 3,4-diethylpyrrole-2-carboxylate, a versatile precursor for pyrrole-based macrocycles and chromophores

Results in Chemistry

Jonathan L. Sessler¹  Adam C. Sedgwick²  Axel Steinbrueck²  Michael Y. Zhao²  James T. Brewster, II² 

[1] Corresponding author.;Department of Chemistry, The University of Texas at Austin, 105 East 24th Street-Stop A5300, Austin, TX 78712-1224, United States;

关键词: Pyrroles;    Synthesis;    Porphyrin building blocks;    Decagram scale;   

DOI  :  

来源: DOAJ

【 摘 要 】

Herein, we describe a detailed preparation of the versatile pyrrole building block 3,4-diethylpyrrole-2-carboxylate (1), a key structural feature in various porphyrins, porphyrinoids, and other chromophores. 1 was prepared via a one-pot DBU catalyzed Henry reaction and acid catalyzed acetylation followed by an aqueous workup and telescoping through an adapted Magnus-Schöllkopf-Barton-Zard cyclization protocol from commercial starting materials. The three-step preparation utilized new chemistry, requires only one formal purification step, and affords 1 at 86% yield and >99% purity on a decagram scale.

【 授权许可】

Unknown