3-Nitrobenzeneboronic acid as an efficient and environmentally benign catalyst for the selective transesterification of β-keto esters

Synlett

Volumn , Issue 3, 2006, Pages 415-418

  Tale, R H ^a   Sagar, A D ^a   Santan, H D ^a   Adude, R N ^a  

^a SWAMI RAMANAND TEERTH MARATHWADA UNIVERSITY   (India)

Author keywords

keto esters; 3 Nitrobenzeneboronic acid; Environmentally benign; Selective reaction

Indexed keywords

BETA KETO ESTER DERIVATIVE; BORONIC ACID DERIVATIVE; ESTER DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; TRANSESTERIFICATION;

EID: 33344467684     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-932454     Document Type: Article

References (33)

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. Org. Synth., Coll. Vol. 3; Wiley: New York, 1955, 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.; Neckersw, 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.; Keshvaraja, 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., Synop. 1996, 426.
22. (a) Carrol, M. J. J. Chem. Soc. 1940, 704.
23. (b) Kimel, W.; Cope, A. C. J. Am. Chem. Soc. 1943, 65, 1992.
24. Tale, R. H.; Patil, K. M. Tetrahedron Lett. 2002, 43, 9715.
25. Tale, R. H.; Patil, K. M.; Dapurkar, S. E. Tetrahedron Lett. 2002, 43, 3427.
26. Sagar, A. D.; Tale, R. H.; Adude, R. N. Tetrahedron Lett. 2003, 44, 70.
27. (a) Carool, M. F. J. Chem. Soc. 1940, 784.
28. (b) Kimel, W.; Cope, A. J. Am. Chem. Soc. 1943, 65.
29. Chavan, S. P.; Zubaidha, P. K.; Dhantale, S. W.; Keshavaraja, A.; Ramaswamy, A. V.; Ravindranathan, T. Tetrahedron Lett. 1996, 37, 233.
30. Camppbell, D. S.; Lawrie, C. W. J. Chem. Soc., Chem. Commun. 1971, 35.
31. Boron, Metallo-Boron Compounds and Boranes; Adams, R. M., Ed.; Wiley: New York, 1964, 693;
32. data quoted in Registry of Toxic Effects of Chemical Substances, NIOSH, 2001.
33. Typical Procedure (Table 1, entry 8): Ethyl acetoacetate (5 mmol), 3-nitrobenzyl alcohol (5 mmol) and 3-nitrobenzeneboronic acid (21 mg, 2.5 mol%) in 20 mL of toluene was heated at reflux for the time allotted (Table 1) with removal of toluene-ethanol azeotrope by distillation. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was concentrated and the residue was chromatographed on silica gel (elution with EtOAc-hexane; 20:80) to afford the pure 3-nitrobenzyl acetoacetate.