Chemistry of (Glycidyloxy)propiolactones. An Intramolecular Transfer of Alkoxy Group in the Alcoholysis and Reduction Reactions

Article abstract of DOI:10.1021/jo00187a025

An interesting intramolecular transfer of an acetal alkoxy group is observed in the alkaline alcoholysis and in reduction by LiAlH4 of α-methyl-α-((1-tert-butoxy-2-methyl-2,3-epoxypropyl)oxy)-β-propiolactone (3a).With either methanol or ethanol and NaOH at 30 deg C, the (glycidyloxy)propiolactone 3a cleaves to produce α-methylglycidaldehyde and either methyl or ethyl α-tert-butoxy-β-hydroxyisobutyrate.Reduction with LiAlH4 at 30 deg C also cleaves 3a, this time with partial reduction to give 2-methyl-2,3-epoxypropanol (6) and 2-methyl-2-tert-butoxypropane-1,3-diol (7).In each case the tert-butoxy group has been transferred to the α carbon of the β-lactone portion of 3a.