2-Ethoxy-5-alkyl-3,4-dihydro-2H-pyrans in Organic Synthesis: A New Convenient Route to Branched δ-Ethoxy Alcohols

Article abstract of DOI:10.1021/jo00176a019

The reaction between 2-ethoxy-5-alkyl-5,6-dichlorotetrahydropyrans and Grignard reagents has been investigated, and the overall results clearly indicate that the reaction provides a useful route to the preparation of highly branched primary, secondary, and tertiary δ-ethoxy alcohols.Experimental evidence is presented to support the occurrence of suitable epoxides as reaction intermediates that may evolve to products either through a pinacol-type isomerization and/or via a cyclic intramolecular rearrangement of a halohydrin halomagnesium salt.