Novel synthesis of vinyl ethers

WCC 15

Katherine R Davis, davis48@tcnj.edu and David A Hunt, hunt@tcnj.edu. Department of Chemistry, The College of New Jersey, 2000 Pennington Rd, Ewing, NJ 08628
A straightforward method for the synthesis of 2-arylvinyl methyl ethers has been developed which avoids the use of the Wittig reaction and the removal of the corresponding phosphorous by-products. The first reaction step converts an aryl ketone to a glycidic ester via a Darzen's condensation. The ester is then hydrolyzed to form a carboxylate salt which, upon acidification, provides the penultimate aryl alkyl-substituted acetalaldehyde. An acid-catalyzed reaction with methanol with concomitant in situ removal of methanol affords the vinyl ether in good yields. These compounds are key intermediates in the preparation of biologically active compounds.
 

The Merck Index Women in Chemistry
2:30 PM-4:30 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Poster

Women Chemists Committee

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009