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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 9: 1975 - 1981

DOI: https://doi.org/10.6023/cjoc201302018

Articles

Etherification of 2-Acetoxymethylpyrrole Derivative with Alcohol Catalyzed by para-Toluenesulfonic Acid

  • Yan Zhaohua ,
  • Yu Xinquan ,
  • Liu Yongjie ,
  • Xu Yun ,
  • Lin Sen
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  • Department of Chemistry, Nanchang University, Nanchang 330031

Received date: 2013-03-01

  Revised date: 2013-04-28

  Online published: 2013-05-08

Supported by

Project supported by the Natural Science Foundation of Jiangxi Province (No. 2009GZH0078)

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Abstract

Etherification of 2-acetoxymethylpyrrole derivatives with alcohols catalyzed by para-toluenesulfonic acid was investigated in details resulting in the smooth formation of the corresponding 2-alkoxymethylpyrrole derivatives in excellent yields. An alternate method for the preparation of 2-alkoxymethylpyrrole derivatives starting from 2-acetoxymethylpyrrole derivatives under weak acidic condition was provided. The main advantages of the developed methodology are mild reaction conditions, high yields of products and simple work-up procedure. A plausible mechanism involving the generation of highly reactive azafulvene intermediate 4 was proposed to explain the observed phenomena.

Key words： 2-acetoxymethylpyrrole derivative; 2-alkoxymethylpyrrole derivative; etherification; azafulvene; alcohol

Cite this article

Yan Zhaohua , Yu Xinquan , Liu Yongjie , Xu Yun , Lin Sen . Etherification of 2-Acetoxymethylpyrrole Derivative with Alcohol Catalyzed by para-Toluenesulfonic Acid[J]. Chinese Journal of Organic Chemistry, 2013 , 33(9) : 1975 -1981 . DOI: 10.6023/cjoc201302018

References

[1] Jean, W.-S.; Kim, E. R.; Chin, Y.-W.; Kim, J. Nat. Prod. Sci. 2011, 17(3), 181.
[2] Liang, Y.; Xu, X.; Xie, H.; Lin, Q.; Wei, X. J. Trop. Subtrop. Bot. 2010, 18(5), 564 (in Chinese).
(梁耀光, 徐新亚, 谢海辉, 林青, 魏孝义, 热带亚热带植物学报, 2010, 18(5), 564.)
[3] Liu, L.; Yang, J.; Shi, Y. J. J. Asian Nat. Prod. Res. 2011, 13(10), 920.
[4] Taniguchi, M.; Soares, A. R. M.; Chandrashaker, V.; Lindsey, J. S. New J. Chem. 2012, 36(4), 1057.
[5] Kinoshita, H.; Tanaka, S.; Nishimori, N.; Dejima, H.; Inomata, K. Bull. Chem. Soc. Jpn. 1992, 65(10), 2660.
[6] Kinoshita, H.; Tanaka, S.; Inomata, K. Chem. Lett. 1989, (7), 1107.
[7] Padwa, A.; Fryxell, G. E.; Gasdaska, J. R.; Venkatramanan, M. K.; Wong, G. S. K. J. Org. Chem. 1989, 54(3), 644.
[8] Silva, M. R.; Sobral A. J.; Silva, J. A. J. Chem. Crystallogr. 2007, 37, 695.
[9] Dinsmore, A.; Mandy, K.; Michael, J. P. Org. Biomol. Chem. 2006, 4(6), 1032.
[10] Yan, Z.; Yu, Z.; Liu, Y.; Hu, W. Chin. J. Org. Chem. 2012, 32, 1965 (in Chinese).
(严兆华, 余章昕, 刘永杰, 胡伟. 有机化学, 2012, 32, 1965.)
[11] Montforts, F. P.; Schwartz, U. M. Liebigs Ann. Chem. 1985, 2301.
[12] Smith, J. A.; Ng, S.; White, J. Org. Biomol. Chem. 2006, 4(12), 2477.
[13] Silverstein, R. M.; Ryskiewicz, E. E. J. Org. Chem. 1955, 20(5), 668.
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