Generation of stable synthetic equivalents of unstable α-alkoxyacetaldehydes: An improved preparation of dirithromycin

Article abstract of DOI:10.1055/s-1993-26006

Described is the in situ preparation of the hemiacetals of α-alkoxyacetaldehydes. The hemiacetals are generated by hydrolysis of an acetal precursor in aqueous acetonitrile solutions. These hemiacetals serve as stable aldehyde equivalents, thus circumventing the production and isolation of unstable α-alkoxyaldehydes. The hemiacetal of 2-methoxyethoxyacetaldehyde is utilized in an effective and efficient preparation of Dirithromycin (LY237216).