795274-98-5Relevant articles and documents
Acid-catalyzed reactions of aromatic aldehydes with ethyl diazoacetate: An investigation on the synthesis of 3-hydroxy-2-arylacrylic acid ethyl esters
Dudley, Matthew E.,Morshed, Monzur,Brennan, Courtney L.,Islam, M. Shahidul,Ahmad, M. Syarhabil,Atuu, Mary-Rose,Branstetter, Bryan,Hossain, M. Mahmun
, p. 7599 - 7608 (2007/10/03)
Several commercial Lewis acids, including those of the Bronsted type, specifically HBF4·OEt2, are able to catalyze the reaction between aromatic aldehydes and ethyl diazoacetate to produce 3-hydroxy-2-arylacrylic acid ethyl esters and 3-oxo-3-arylpropanoic acid ethyl esters. Reactions catalyzed by the iron Lewis acid [(η5-C 5H5)Fe+(CO)2(THF)]BF 4- (i.e., 1) have the best yields and greatest ratio of 3-hydroxy-2-arylacrylic acid ethyl ester. The product distribution of 1 is not affected in the presence of Proton Sponge, but is dependent on temperature and the nature of the substrate aldehyde, whereas the activity of HBF 4-OEt2 is affected by the presence of Proton Sponge and is reactive at temperatures as low as -78 °C. Consequently, both 1 and HBF4·OEt2 are valuable catalysts in producing important 3-hydroxy-2-arylacrylic acid ethyl esters as precursors to biologically active compounds.
