405219-10-5Relevant academic research and scientific papers
Diethoxymethyl protected pyrroles: Synthesis and regioselective transformations
Bergauer,Gmeiner
, p. 2281 - 2288 (2007/10/03)
Treatment of the acceptor-substituted pyrroles 1a-k with neat triethyl orthoformate gives access to the diethoxymethyl (DEM) protected derivatives 2a-k in high yield. Convenient and mild cleavage was achieved by subsequent treatment of the DEM-pyrroles 2a-k with trifluoroacetic acid in acetonitrile and aqueous NaOH at room temperature. DEM protection proved suitable for a variety of regioselective transformations involving directed orthometalation and iodine-magnesium exchange processes. Furthermore, electrophilic halogenations and Pd-catalyzed coupling reactions were also carried out.
