Synthesis of substituted 3-(triisopropylsilyl)-2-naphthols

ORGN 52

Hélène Juteau1, Yves Gareau1, and Hugo Lachance2. (1) Department of Medicinal Chemistry, Merck Frosst Center for Therapeutic Research, P.O. Box 1005, Pointe Claire-Dorval, QC H9R 4P8, Canada, (2) Department of Chemistry, University of Alberta, Edmonton, AB T6G 2G2, Canada
Naphthol derivatives are important intermediates used for the preparation of pharmaceuticals, agrochemicals, and polycyclic compounds. They have also been extensively used as chiral auxiliaries. Very few examples can be found in the literature for the preparation of 2-naphthol. Herein we wish to describe a new procedure for the preparation of polysubstituted 2-naphthols by the condensation of phenylacetyl chloride derivatives and trialkylsilyl acetylenes catalyzed by aluminum chloride (scheme 1). The reactions were totally regioselective and gave only the 3-(trialkylsilyl)-2-naphthol isomers (41 to 67% yield). The remaining trialkylsilyl group can also be used as a handle for further functionalization.

Scheme 1

 

New Reactions and Methodology, Metal-Mediated Reactions, Heterocycles and Aromatics
8:00 PM-10:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- Hall A, Poster

Division of Organic Chemistry

The 227th ACS National Meeting, Anaheim, CA, March 28-April 1, 2004