Preparation of substituted 2-naphthols

ORGN 655

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
We have developed a simple method for the synthesis of substituted 2-naphthols based on a silyl protected acetylene. The addition of triisopropylsilylacetylene to a mixture of AlCl3 and the desire ArCH2C(O)Cl in dichloromethane resulted in the formation of 3-(triisopropylsilyl)-2-naphthol in 41-67% yield.