A novel direct conversion of primary amides to their corresponding methyl esters

European Journal of Organic Chemistry

Volumn , Issue 6, 2007, Pages 1026-1030

  Li, Ang Chun ^a,b   Ren, Jie ^a   Liao, Tou Gen ^a,b   Jiang, Ju Xing ^a,b   Zhu, Hua Jie ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

Amides; Density functional calculations; Esters; Reaction mechanisms

Indexed keywords

EID: 34250616379     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600853     Document Type: Article

References (30)

1. R. M. Propst III, L. S. Trzupek, J. Am. Chem. Soc. 1981, 103, 3233-3235.
2. A. Solladié-Cavallo, M. Bencheqroun, J. Org. Chem. 1992, 57, 5831-5834.
3. J. J. Hans, R. W. Driver, S. D. Burke, J. Org. Chem. 1999, 64, 1430-1431.
4. X. Huang, G. Y. Wang, Z. C. Chen, Newly Edited Chemistry of Organic Synthesis, Chemical Industry Publisher, Beijing, 2005, pp. 478-480. For examples of primary amides to acids, see: pp. 380-382.
5. E. H. White, J. Am. Chem. Soc. 1954, 76, 4497-4498.
6. E. H. White, C. A. Elliger, J. Am. Chem. Soc. 1967, 89, 165-167.
7. W. J. Le Noble, E. H. White, P. M. Dzadzic, J. Am. Chem. Soc. 1976, 98, 4020-4221.
8. D. M. Shendage, R. Fröhlich, G. Haufe. Org. Lett. 2004, 6, 3675-3678.
9. D. T. Glatzhofer, R. R. Roy, K. N. Cossey, Org. Lett. 2002, 4, 2349-2352.
10. R. W. Darbeau, E. V. Perez, J. I. Sobieski, W. A. Rose, M. C. Yates, B. J. Boese, N. R. Darbeau, J. Org. Chem. 2001, 66, 5679-5686.
11. For ion-exchange resin uses in the conversion, see: W. L. Greenlee, E. D. Thorsett, J. Org. Chem. 1981, 46, 5351-5353.
12. a) H. A. Taylor, T. W. Davis, J. Phys. Chem. 1928, 32, 1467-1480;
13. b) E. Emmet Reid, Am. Chem. J. 1909, 41, 483-510.
14. IV catalyzed conversion, see: L. E. Fisher, J. M. Caroon, S. R. Stabler, S. Lundberg, S. Zaidi, Can. J. Chem. 1994, 72, 142.
15. For chlorotrimethylsilane use in the transformation of amides into esters, see: C.-H. Xue, F.-T. Luo, J. Chin. Chem. Soc. (Taipei) 2004, 51, 359.
16. [11] in the Supporting Information.
17. See Supporting Information for reaction details.
18. W. L. Xiao, H. J. Zhu, Y. H. Shen, R. T. Li, S. H. Li, H. D. Sun, Y. T. Zheng, R. R. Wang, Y. Lu, C. Wang, Q. T. Zeng, Org. Lett. 2005, 7, 2145.
19. H. J. Zhu, J. X. Jiang, S. Saobo, C. U. Pittman Jr, J. Org. Chem. 2005, 70, 261-267.
20. L. C. Li, J. X. Jiang, J. Ren, Y. Ren, C. U. Pittman Jr, H. J. Zhu, Eur. J. Org. Chem. 2006, 1981-1990.
21. M. J. Frisch, G. W. Trucks, H. B. Schlegel, Gaussian 03 User's Reference, Gaussian Inc., Carnegie, PA, 2003..
22. S. Mirertus, E. Scrocco, J. Tomasi, Chem. Phys. Lett. 1996, 255, 327.
23. M. Cossi, V. Barone, J. Mennucci, J. Tomasi, Chem. Phys. Lett. 1998, 286, 253.
24. J. Tomasi, B. Mennucci, E. Cances, J. Mol. Struct.: THEOCHEM 1999, 464, 211.
25. M. Cossi, G. Scalmani, N. Rega, V. Barone, J. Chem. Phys. 2002, 117, 43.
26. C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1989, 90, 2154.
27. C. Gonzalez, H. B. Schlegel, J. Chem. Phys. 1990, 94, 5523.
28. 4-benzo[e][1,2,3]oxathiazin-4-one.
29. Experiments were performed to define the smallest mol ratio of MeOH/acetamide where 6 would still be formed. However, because the methyl acetate formed has a low boiling point, further studies to determine the yields were not performed.
30. See the Supporting Information for reaction details.