A novel synthesis of reducing 3-hydroxy aryl propenoic acid ester to aryl propenoic acid ester

ORGN 589

Muhammad Syarhabil Ahmad, M. Mahmun. Hossain, and Mohammad Shahid Islam. University of Wisconsin-Milwaukee, 3210 N. Cramer Street, Milwaukee, WI 53211
The formation of a propenoic acid ester by a single step reaction of 3-hydroxy aryl propenoic acid ester was observed in high yield. This unprecedented one step reduction of the 3-hydroxy aryl propenoic acid esters is an important reaction for the precursors of several anti inflammatory drugs. As an example, 2-(6-methoxy-2-naphtyl)-propenoic acid acid, a precursor of the drug Naproxen, was recently synthesized in three simple steps from commercially available starting aldehyde in very good yields. Several other examples of this type of reduction will be presented along with a plausible mechanism.