Skip to main content
SpringerLink
Log in

Cesium carbonate as efficient catalyst for chemoselective transesterification of β-ketoesters under conventional and unconventional conditions

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Transesterification of β-ketoesters with different alcohols has been studied under conventional and unconventional conditions using the simple desktop chemical cesium carbonate as catalyst. These methods enabled transesterification of β-ketoesters in good yields with dramatic rate acceleration and reduced reaction times. The procedures which used unconventional methods, for example sonication and microwave irradiation, are highly promising compared with conventional procedures.

Graphical Abstract

Scheme 1 General Equation for a transesterification reaction

Scheme 2 Transesterification of β-ketoesters

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Scheme 2

Similar content being viewed by others

References

  1. R.C. West (ed.), CRC Handbook of Chemistry and Physics, 62nd edn. (CRC Press, Boca Raton, 1981). p. B-91. ISBN 0-8493-0462-8

  2. D.R. Lide (ed.), Handbook of Chemistry and Physics, 83rd edn. (CRC Press LLC, Boca Raton, 2002–2003)

  3. C. Galli, Org. Prep. Proced. Int. 24, 287 (1992)

    Article  Google Scholar 

  4. J.A. Cella, S.W. Bacon, J. Org. Chem. 49, 1122 (1984)

    Article  CAS  Google Scholar 

  5. J.P. Wolfe, S.L. Buchwald, J. Org. Chem. 65, 1144 (2000)

    Article  CAS  Google Scholar 

  6. G. Dijkstra, W.H. Kruizinga, R.M. Kellogg, J. Org. Chem. 52, 4230 (1987)

    Article  CAS  Google Scholar 

  7. M. Escudero, L.D. Kremenchuzky, I.A. Perillo, H. Cerecetto, M. Blanco, Synthesis 4, 571 (2010)

    Google Scholar 

  8. B.U.W. Maes, K.T.J. Loones, T.H.M. Jonckers, G.L.F. Lemière, R.A. Dommisse, A. Haemers, Synlett 12, 1995 (2002)

    Article  Google Scholar 

  9. M. Catellani, C. Catucci, G. Celentano, R. Ferraccioli, Synlett 6, 803 (2001)

    Article  Google Scholar 

  10. R.N. Salvatore, A.S. Nagle, K.W. Jung, J. Org. Chem. 67, 674 (2002)

    Article  CAS  Google Scholar 

  11. S.W. Wright, D.L. Hageman, L.D. McClure, J. Org. Chem. 59, 6095 (1994)

    Article  CAS  Google Scholar 

  12. E. Maerten, F. Hassouna, S. Couve-Bonnaire, A. Mortreux, J.F. Carpentier, Y. Castanet, Synlett 12, 1874 (2003)

    Google Scholar 

  13. J.P. Parrish, B. Sudaresan, K.W. Jung, Synth. Commun. 29, 4423 (1999)

    Article  CAS  Google Scholar 

  14. R. Gujadhur, D. Venkataraman, J.T. Kintigh, Tetrahedron Lett. 42, 4791 (2001)

    Article  CAS  Google Scholar 

  15. T. Sato, J. Otera, Synlett 4, 336 (1995)

    Article  Google Scholar 

  16. M.T. Honaker, J. Sandefur, J.L. Hargett, A.L. McDaniel, R.N. Salvatore, Tetrahedron Lett. 44, 8373 (2003)

    Article  CAS  Google Scholar 

  17. Y.J. Wu, H. He, Synlett 12, 1789 (2003)

    Article  Google Scholar 

  18. A. Kondoh, H. Takami, H. Yorimitsu, K. Oshima, J. Org. Chem. 70, 6468 (2005)

    Article  CAS  Google Scholar 

  19. B. Karimi, F.K. Estanhani, R. Soc. Chem. 55, 5556 (2009)

    Google Scholar 

  20. L. Lie, G. Rao, H.L. Sun, J.L. Zhang, Adv. Synth. Catal. 352, 2371 (2010)

    Article  Google Scholar 

  21. J.S. Witzemann, W.D. Nottingham, J. Org. Chem. 54, 2815 (1989)

    Google Scholar 

  22. J. Otera, Chem. Rev. 93, 1449 (1993)

    Article  CAS  Google Scholar 

  23. L. Hintermann, A. Togni, Helv. Chim. Acta 83, 2425 (2000)

    Article  CAS  Google Scholar 

  24. X.-C. He, B. Wang, G. Yu, D. Bai, Tetrahedron Asymmetry 12, 3213 (2001)

    Article  CAS  Google Scholar 

  25. T. Sugimura, S. Nakagawa, A. Tai, Bull. Chem. Soc. Jpn. 75, 355 (2002)

    Article  CAS  Google Scholar 

  26. D. Franco, A. Riahi, F. Henin, J. Muzart, E. Dunach, Eur. J. Org. Chem. 14, 2257 (2002)

    Article  Google Scholar 

  27. N. Nishiwaki, D. Nishida, T. Ohnishi, F. Hidaka, S. Shimizu, M. Tamura, K. Hori, Y. Tohda, M. Ariga, J. Org. Chem. 68, 8650 (2003)

    Article  CAS  Google Scholar 

  28. K. Majima, R. Takita, A. Okada, T. Ohshima, M. Shibasaki, J. Am. Chem. Soc. 125, 15837 (2003)

    Article  CAS  Google Scholar 

  29. C.A.M. Fraga, L.H.P. Teixeira, C.M.S. Menezes, C.M.R. Sant Anna, M.C.K.V. Ramos, F.R. Aquino Neto, E. Barreiro, Tetrahedron 60, 2745 (2004)

    Article  CAS  Google Scholar 

  30. M. Gianotti, G. Martelli, G. Spunta, E. Campana, M. Panunzio, M. Mendozza, Synth. Commun. 30, 1725 (2000)

    Article  CAS  Google Scholar 

  31. J. Otera, Chem. Rev. 93, 1449 (1993)

    Article  CAS  Google Scholar 

  32. S. Benetti, R. Romagnoli, C. De Risi, S. Giampiera, Z. Vinicio, Chem. Rev. 95, 1065 (1995)

    Article  CAS  Google Scholar 

  33. G. Krishnaiah, B. Sandeep, D. Kondhare, K.C. Rajanna, J.N. Reddy, Y.R. Rao, P.K. Zhubaidha, Tetrahedron Lett. 54, 703 (2013)

    Article  CAS  Google Scholar 

  34. M. Bender, J. Figuera, J. Am. Chem. Soc. 75, 6304 (1953)

    Article  CAS  Google Scholar 

  35. D. Bradley, R.C. Mehrotra, I. Rothwell, A. Singh, Alkoxo and Aryloxo Derivatives of Metals (Academic Press, San Diego, 2001)

    Google Scholar 

  36. T.G. Leighton, The Acoustic Bubble (Academic, London, 1994)

    Google Scholar 

  37. E.B. Flint, K.S. Suslick, Science 253, 1397 (1991)

    Article  CAS  Google Scholar 

  38. W.B. McNamara, Y. Didenko, K.S. Suslick, in Sonochemistry and Sonoluminescence, Proceedings of the NATO Advanced Study Institute, Series C, vol 524 (Kluwer, Dordrecht, 1999)

  39. K.S. Suslick (ed.), Ultrasound: Its Chemical, Physical, and Biological Effects (VCH, New York, 1988)

    Google Scholar 

  40. S.M. Haile, D.W. Johnson, G.H. Wiseman, H.K. Bowen, J. Am. Ceram. Soc. 72, 2004 (1989)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors are indebted to CSIR, New Delhi (India) and UGC (New Delhi) for financial support in the form of an SRF Fellowship to G. Krishnaiah and a JRF Fellowship to P. Srinivas. The authors gratefully acknowledge constant encouragement and moral support rendered by Professor P.K. Saiprakash (Former Dean, Faculty of Science OU) and Professor T. Navaneeth Rao (Former Vice-Chancellor, OU; Principal, Nizam College and Head, Department of Chemistry, O.U).

Author information

Authors and Affiliations

  1. Department of Chemistry, Osmania University, Hyderabad, 500 007, AP, India

    G. Krishnaiah, K. C. Rajanna, K. Rajendar Reddy, M. Satish Kumar & P. Srinivas

  2. Department of Chemistry, Rajiv Gandhi University of Knowledge Technologies, IIIT, Basara, AP, India

    Y. Rajeshwer Rao

Authors
  1. G. Krishnaiah
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. K. C. Rajanna
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. K. Rajendar Reddy
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. Satish Kumar
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. P. Srinivas
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Y. Rajeshwer Rao
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to K. C. Rajanna.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Krishnaiah, G., Rajanna, K.C., Reddy, K.R. et al. Cesium carbonate as efficient catalyst for chemoselective transesterification of β-ketoesters under conventional and unconventional conditions. Res Chem Intermed 41, 2739–2751 (2015). https://doi.org/10.1007/s11164-013-1383-x

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-013-1383-x

Keywords

Search

Navigation