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

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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.

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Authors
  1. V. A. Slavinskaya
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  2. Dz. É. Sile
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  3. N. G. Panchenko
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  4. É. Kh. Korchagova
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  5. G. F. Rozental'
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  6. Yu. Yu. Balodis
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  7. I. V. Turovskis
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  8. S. Kh. Grinberga
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  9. E. Lukevics
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Additional information

Latvian Institute of Organic Synthesis, Riga, Latvia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1329–1334, October, 1998.

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Slavinskaya, V.A., Sile, D.É., Panchenko, N.G. et al. Hydrogenation of derivatives of 2-oxo-4-(2-thienyl)butenoic acid at palladium and nickel catalysts. Chem Heterocycl Compd 34, 1127–1131 (1998). https://doi.org/10.1007/BF02319489

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  • DOI: https://doi.org/10.1007/BF02319489

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