The preparation of 3-alkylthio-2-methoxytetrahydropyrans
- 1 June 1967
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 45 (11) , 1195-1200
- https://doi.org/10.1139/v67-198
Abstract
The reaction of alkylsulfenyl chlorides with 3,4-dihydro-2H-pyran, followed by treatment of the product with sodium methoxide, gave, highly stereoselectively, trans-3-alkylthio-2-methoxytetrahydropyrans. Purification by distillation under a vacuum at temperatures above 55° resulted in the elimination of methyl alcohol to produce 5-(alkylthio)-3,4-dihydro-2H-pyrans in a good yield. At lower temperatures, the more volatile homologues could be distilled undecomposed, but these had undergone thermal isomerization to a mixture of cis- and trans-3-alkylthio-2-methoxytetrahydropyrans. The conformational preference of these isomers is discussed.Keywords
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