Synthesis of Alkyl 4-Hydroxy-2-alkynoates

Article abstract of DOI:10.1021/jo01289a006

The lithium acetylide anion of ethyl or methyl propiolate is readily prepared by the addition of n-butyllithium to ethyl or methyl propiolate at low temperature.The anion rapidly adds to a variety of aldehydes or ketones to give ethyl or methyl 4-hydroxy-2-alkynoates in high yield.