Synthesis of Pyrroles from Benzyl Isocyanoacetate

Authors:
  • TLTimothy D. Lash
    Timothy D. Lash
  • JBJohn R. Bellettini
    John R. Bellettini
  • JBJolie A. Bastian
    Jolie A. Bastian
  • KCKendall B. Couch
    Kendall B. Couch

Abstract
Benzyl esters of 5-unsubstituted pyrrole-2-carboxylic acids were prepared in excellent yields by the base-catalyzed condensation of benzyl isocyanoacetate with α-acetoxynitro compounds, or nitroalkenes,in refluxing tetrahydrofuran. These pyrrolic products are important intermediates in the synthesis of porphyrins and related compounds.