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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
O-Thien-2-yl Esters: A Synthetic Approach to a Rare Class of Materials Using a Modified Steglich Esterification
Anthony V Bertolino1, Megan A Sroka1, Emily P Richards1
1Department of Chemistry and Biochemistry, Kent State University, Kent, Ohio 44242-0001, United States.
Abstract:
Herein, we describe a simple procedure for the transformation of 3-thien-2-one to O-thien-2-yl esters via modified Steglich esterification. Attempted esterification using standard Steglich conditions gave low yields due to a competing O-N acyl migration, resulting in the formation of N-acylurea as the major product. The addition of a catalytic amount of p-TSA·H2O eliminates the formation of the N-acylurea. Various O-thien-2-yl esters have been synthesized using this procedure in yields of 51-85%.
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