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An unexpected Pummerer rearrangement in the synthetic route to ethyl (2′-hydroxy-4′,5′-methylenedioxyphenyl)acetate: An alternative approach to 2,3-dimethylthio benzofurans

Author:
Carreño-Montero, Ariel, Maldonado, Luis A., Chávez, María Isabel, Hernández-Ortega, Simón, Delgado, Guillermo
Source:
Tetrahedron letters 2019
ISSN:
0040-4039
Subject:
aromatic compounds, benzofurans, catalysts, catalytic activity, chemical structure, coumarin, ethanolysis, glycemic effect, organic sulfur compounds
Abstract:
The synthesis of ethyl (2′-hydroxy-4′,5′-methylendioxophenyl)acetate, a fragment of the antihyperglycemic natural coumarin subcoriacin, is reported. We found an expeditious route to the title compound in five steps. Final metal catalyzed acid ethanolysis of the vinylic 1,1-methylthio methylsulfoxide derivative afforded the required aryl acetic ester, but in the absence of metal catalyst, an unexpected Pummerer rearrangement produced the 2,3-dimethylthiofuran derivative as the major product. This last result provides an alternative entry to 2,3-dimethlythiobenzofurans.
Agid:
6729761