Abstract
The application of heterogeneous catalysis and green solvents to the set up of widely employed reactions is a challenge in contemporary organic chemistry. We applied such an approach to the synthesis and further conversion of tetrahydropyranyl ethers, an important class of compounds widely employed in multistep syntheses. Several alcohols and phenols were almost quantitatively converted into the corresponding tetrahydropyranyl ethers in cyclopentyl methyl ether or 2-methyltetrahydrofuran employing NH4HSO4 supported on SiO2 as a recyclable acidic catalyst. Easy work up of the reaction mixtures and the versatility of the solvents allowed further conversion of the reaction products under one-pot reaction conditions.
Highlights
Due to their general stability to a wide range of reagents and ease of removal, tetrahydropyranyl (THP) ethers are widely employed in multistep organic synthesis for the protection of hydroxy derivatives [1,2]
A lot of work has been devoted to the search of low impact, heterogeneous and recyclable catalysts to promote THP ethers synthesis [2,8,9,10,11,12,13,14], to the best of our knowledge no attention was dedicated to their employment in low impact solvents
Matic example of the ironic Murphy’s Law of Solvents, recently stated by Jessop et al [16]: “The best solvent for any process step is bad for the step”. Starting from these premises and following our interest in the development of reaction procedures in low impact solvents [17,18], we report here on the tetrahydropyranylation of alcohols and phenols in cyclopentyl methyl ether (CPME) and 2-methyltetrahydrofuran (2-MeTHF) in the presence of heterogeneous acidic catalysts
Summary
Due to their general stability to a wide range of reagents and ease of removal, tetrahydropyranyl (THP) ethers are widely employed in multistep organic synthesis for the protection of hydroxy derivatives [1,2]. Starting from these premises and following our interest in the development of reaction procedures in low impact solvents [17,18], we report here on the tetrahydropyranylation of alcohols and phenols in cyclopentyl methyl ether (CPME) and 2-methyltetrahydrofuran (2-MeTHF) in the presence of heterogeneous acidic catalysts.
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