Synthesis of α- and β-branched ethers from alcohols by reaction of acetals with Grignard reagents: Synthesis of isopropyl and isobutyl ethers of (1S*,2R*S*,4R*)-6-methylenebicyclo[2.2.2]octan-2-ol

Timothy M. Willson, Jack Amburgey, Scott E. Denmark

Research output: Contribution to journalArticle

Abstract

Non-symmetrical acetals have been combined with Grignard reagents in toluene at reflux to generate α-and β-branched ethers in moderate to high yields. The synthesis of isopropyl and isobutyl ethers of the bicyclic alcohol 1 was accomplished using this methodology, although reactions in the synseries were complicated by the formation of tricyclic products by an intramolecular cyclisation. The scope and limitations of the ether-forming reactions were explored with a series of acetals derived from primary, secondary and tertiary alcohols. The halide component of the Grignard reagent and the solvent were found to be an important factor in facilitating these reactions.

Original languageEnglish (US)
Pages (from-to)2899-2906
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
StatePublished - Dec 1 1991

    Fingerprint

ASJC Scopus subject areas

  • Chemistry(all)

Cite this