65818-36-2Relevant academic research and scientific papers
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-Methylenebicyclooctan-2-ol
Willson, Timothy M.,Amburgey, Jack,Denmark, Scott E.
, p. 2899 - 2906 (2007/10/02)
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 syn-series 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.
