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Synthesis 1993; 1993(11): 1089-1091
DOI: 10.1055/s-1993-26006
short paper
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Generation of Stable Synthetic Equivalents of Unstable α-Alkoxyacetaldehydes: An Improved Preparation of Dirithromycin

John M. Mcgill*
  • *Lilly Research Laboratories, Eli Lilly and Company, Lafayette, Indiana 47902, USA
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Publication Date:
29 April 2002 (online)

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Described is the in situ preparation of the hemiacetals of α-alkoxy-acetaldehydes. 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).