Diethoxymethyl Protected Pyrroles: Synthesis and Regioselective Transformations

Gmeiner P (2001)


Publication Type: Journal article

Publication year: 2001

Journal

Publisher: Thieme Publishing / Georg Thieme Verlag

Pages Range: 2281-2288

DOI: 10.1055/s-2001-18445

Abstract

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.

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How to cite

APA:

Gmeiner, P. (2001). Diethoxymethyl Protected Pyrroles: Synthesis and Regioselective Transformations. Synthesis-Stuttgart, 2281-2288. https://doi.org/10.1055/s-2001-18445

MLA:

Gmeiner, Peter. "Diethoxymethyl Protected Pyrroles: Synthesis and Regioselective Transformations." Synthesis-Stuttgart (2001): 2281-2288.

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