Hydrogenation of derivatives of 2-oxo-4-(2-thienyl)butenoic acid at palladium and nickel catalysts

Abstract

The hydrogenation of sodium and ethyl 2-oxo-4-(2-thienyl)butenoate at Raney nickel and palladium black was investigated. With Raney nickel the reaction products were the corresponding derivatives of 2-oxo-4-(2-thienyl)butyric acid and 2-hydroxy-4-(2-thienyl)butyric acid and the products from bimolecular condensation. If palladium black is used, the reaction can be directed toward the selective formation of the corresponding derivative of 2-oxo-4-(2-thienyl)butyric acid. The hydrogenation of the salts is more selective than that of the esters. During the hydrogenation of ethyl 2-oxo-4-(2-thienyl)butenoate at palladium black in solution in anhydrous ethanol the ethyl esters of 2-oxo-4-(2-thienyl)butyric and 2-oxo-4-(2-tetrahydrothienyl)butyric acids and the corresponding ketals are formed. The mechanism of the hydrogenation of 4-substituted 2-oxobutenoic acids is discussed.

How to Cite
Slavinskaya, V. A.; Sile, D. É.; Panchenko, N. G.;  Korchagova, É.; Rozental', G. F.; Balodis, Yu. Yu.; Turovskis, I. V.; Grinberga, S. Kh.; Lukevics, E. Chem. Heterocycl. Compd. 1998, 34, 1127. [Khim. Geterotsikl. Soedin. 1998, 34, 1329.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02319489