A facile and selective procedure for transesterification of β-keto esters promoted by yttria-zirconia based lewis acid catalyst

Synlett

Volumn , Issue 2, 2000, Pages 251-253

  Kumar, Pradeep ^a   Kumar Pandey, Rajesh ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

Alcohols; Heterogeneous catalysis; Transesterification; Yttria zirconia based Lewis acid; keto esters

Indexed keywords

ESTER; YTTRIUM; ZIRCONIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION;

EID: 0343049165     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6496     Document Type: Article

References (27)

1. (a) Fujita, T.; Tanaka, M.; Norimine, Y.; Suemune, H. J. Org. Chem. 1997, 62, 3824.
2. (b) Shapiro, G.; Marzi, M. J. Org. Chem. 1997, 62, 7096.
3. (a) Rehberg, C. E.; Fisher, C. H. J. Am. Chem. Soc. 1944, 66, 1203.
4. (b) Rehberg, C. E.; Faucette, W. A.; Fisher, C. H. J. Am. Chem. Soc. 1944, 66, 1723.
5. (c) Rehberg, C. E. Organic Synthesis; Wiley: New York 1955; Collect. Vol. 3, p 146.
6. (d) Haken, J. K. J. Appl. Chem. 1963, 13, 168.
7. (a) Yazawa, H.; Tanaka. K.; Kariyone, K. Tetrahedron Lett. 1974, 3995.
8. (b) Blossey, E. C.; Turner, L. M.; Neckers, D. C. Tetrahedron Lett. 1973, 1823.
9. Taber, D. F.; Amedio, J. C., Jr.; Patel, Y. K. J. Org. Chem. 1985, 50, 3618.
10. (a) Taft, R. W., Jr; Newman, M. S.; Verhoek, F, H. J. Am. Chem. Soc. 1950, 72, 4511.
11. (b) Billman, J. H.; Smith, W. T., Jr.; Rendall, J. L. J. Am. Chem. Soc. 1947, 69, 2058.
12. (a) Osipow, L.; Snell, F. D.; Finchler, A. J. Am. Oil Chem. Soc. 1957, 34, 185.
13. (b) Komori, S.; Okahara, M.; Okamoto, K. J. Am. Oil Chem. Soc. 1960, 37, 468.
14. Witzeman, J. S.; Nottingham, W. D. J. Org. Chem. 1991, 56, 1713.
15. (a) Otera, J.; Yano, T.; Kawabata, A.; Hitoshi, N. Tetrahedron Lett. 1986, 27, 2383.
16. (b) Otera, J.; Danoh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307.
17. Chavan, S. P.; Zubaidha, P. K.; Dantale, S. W.; Keshavaraja, A.; Ramaswamy, A. V.; Ravindranathan, T. Tetrahedron Lett. 1996, 37, 233.
18. (a) Balaji, B. S.; Sasidharan, M.; Kumar, R.; Chanda, M. Chem. Commun. 1996, 707.
19. (b) Balaji, B. S.; Chanda, M. Tetrahedron 1998, 54, 13237.
20. Ponde, D. E.; Deshpande, V. H.; Bulbule, V. J.; Sudalai, A.; Gajare, A. S. J. Org. Chem. 1998, 63, 1058.
21. Pais, G. C. G.; Keshavaraja, A.; Saravanan, K.; Kumar, P. J. Chem Res. (S) 1996, 426.
22. General experimental procedure for transesterification : A mixture of ketoester (1 equiv), alcohol (1 equiv), and catalyst (20% by weight) in toluene (10 equiv) was refluxed for the indicated length of time (Table 1). The reaction was monitored by TLC. After completion of the reaction, the catalyst was filtered and the filtrate was concentrated to get the crude product which was purified by silica gel column chromatography using petroleum ether/ethyl acetate as eluent to afford the pure transesterified product.
23. (a) Carrol, M. F. J. Chem. Soc. 1940, 704.
24. (b) Kimel, W.; Cope, A. C. J. Am. Chem. Soc. 1943, 65, 1992.
25. Campbell, D. S.; Lawrie, C. W. J. Chem. Soc., Chem. Commun. 1971, 355.
26. 2 adsorption techniques. For details, see : Keshavaraja, A.; Hegde, V. R.; Pandey, B.; Ramaswamy, A. V.; Kumar, P.; Ravindranathan, T. Angew. Chem. Int. Ed. Engl. 1995, 34, 2143; U. S. Patent 5,932,752 (1999)
27. +173 (2.39), 143 (100), 135 (1.8), 100 (8.38), 85 (14.97), 74 (6.59), 74 (6.29), 58 (40.72).