Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups?

Green Chemistry Pub Date: 2012-04-02 DOI: 10.1039/C2GC35265F

Abstract

We report a new one-pot synthetic route to tetrahydrofuran derivatives, which were unexpectedly produced under basic conditions by intramolecular etherification of substituted five-membered cyclic carbonates. For alcohols with vicinal hydroxyl groups, and additional OH groups at the β-position, intramolecular etherification leading to 3-hydroxytetrahydrofuran derivatives was observed. These reactions were studied for compounds having from 2 to 6 hydroxyl groups per molecule, and the mechanism was proposed. The developed method provides a new environmentally friendly approach to the synthesis of five-membered cyclic ether derivatives under non-acidic conditions.

Graphical abstract: Intramolecular etherification of five-membered cyclic carbonates bearing hydroxyalkyl groups
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