Base-promoted deacylation of 2-acetyl-2,5-dihydrothiophenes and their oxygen-mediated hydroxylation

Key Points

Deacylation occurs with sodium methoxide, resulting in deacylated products and highlighting its effectiveness in this transformation.
Hydroxylation is achieved using sodium ethoxide in an oxygen-saturated ethanolic solution, producing hydroxy-substituted derivatives.
Solvent choice significantly influences the outcomes of these chemical reactions, emphasizing the importance of chemical environments.
The findings support the versatility of 2-acetyl-2,5-dihydrothiophenes in synthetic organic chemistry, offering new synthetic routes.

Abstract

Solvent-dependent transformations of polysubstituted 2-acetyl-2,5-dihydrothiophenes to the corresponding 2-hydroxy- or deacetylated derivatives are described. The treatment of a methanolic solution of the dihydrothiophene substrates with sodium methoxide afforded the deacylated products. Conversely, the treatment with sodium ethoxide in an oxygen saturated ethanolic solution produced 2-hydroxy substituted 2,5-dihydrothiophenes.

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Cite This Study

Ilkin et al. (Wed,) studied this question.

synapsesocial.com/papers/69a75d4dc6e9836116a2718f https://doi.org/https://doi.org/10.3762/bjoc.22.13

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