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Sonochemical Reformatsky Reaction Using Indium


Abstract

Sonochemical Reformatsky reaction of aldehydes or ketones with ethyl bromoacetate in the presence of indium afforded $\beta-hydroxyesters$ in good to excellent yields under mild conditions. 2- or 3-Hydroxybenzaldehyde that contains an acidic hydrogen r eacted with ethyl bromoacetate to provide the desired compounds with the same efficiency. In the case of ethyl 2-bromopropanoate and ethyl 2-bromo-2-methylpropanoate, the desired products were obtained in good yields. Reaction of aldehyde with indium reagent in the presence of ketone group proceeded chemoselectively.

Keywords

References

  1. Shriner, R. L. Org. React. 1946, 1, 1.
  2. Rathke, M. W. Org. React. 1975, 22, 423.
  3. Gensler, W. J. Chem. Rev. 1957, 57, 265.
  4. Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. https://doi.org/10.1021/cr50025a003
  5. Becker, D.; Brodsky, N.; Kalo, I. J. Org. Chem. 1978, 43, 2557. https://doi.org/10.1021/jo00407a002
  6. Barco, A.; Benett, S.; Pollini, G. P. J. Org. Chem. 1980, 45, 4776. https://doi.org/10.1021/jo01311a047
  7. Klipa, D. K.; Hart, H. J. Org. Chem. 1981, 46, 2815. https://doi.org/10.1021/jo00326a050
  8. West, F. G.; Gunawardena, G. V. J. Org. Chem. 1993, 58, 5043. https://doi.org/10.1021/jo00071a008
  9. Witzemann, J. S.; Nottingham, W. D. J. Org. Chem. 1989, 54, 3258 https://doi.org/10.1021/jo00275a006
  10. March, J. Advanced Organic Chemistry; Wiley: New York, 1992; p 929.
  11. Marioka, K.; Hashimoto, S.; Kitagawa, Y.; Yamamoto, H.; Nozaki, H. J. Am. Chem. Soc. 1977, 99, 7705. https://doi.org/10.1021/ja00465a049
  12. Harada, T.; Mukaiyama, T. Chem. Lett. 1982, 161.
  13. Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904. https://doi.org/10.1021/jo00195a006
  14. Nokami, J.; Tamaoka, T.; Ogawa, H.; Wakabayashi, S. Chem. Lett. 1986, 541.
  15. Shen, Z.; Zhang, J.; Zou, H.; Yang, M. Tetrahedron Lett. 1997, 38, 2733. https://doi.org/10.1016/S0040-4039(97)00456-5
  16. Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363. https://doi.org/10.1016/S0040-4039(96)02494-X
  17. Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 4387. https://doi.org/10.1016/S0040-4039(97)00952-0
  18. Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253. https://doi.org/10.1021/jo00903a031
  19. Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453. https://doi.org/10.1080/00397918808064009
  20. Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291. https://doi.org/10.1016/0022-328X(89)85180-0
  21. Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc. Perkin Trans. 1 1991, 499.
  22. Johar, P. S.; Araki, S.; Butsugan, Y. J. Chem. Soc. Perkin Trans. 1 1992, 711.
  23. Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 1191. https://doi.org/10.1002/anie.199311911
  24. Cahiez, G.; Chavant, P.-Y. Tetrahedron Lett. 1989, 30, 7373. https://doi.org/10.1016/S0040-4039(00)70700-3
  25. Kagan, H. B.; Namy, J.-L.; Girard, P. Tetrahedron 1981, 37, 175. https://doi.org/10.1016/0040-4020(81)85053-3
  26. Tabuchi, T.; Kawamura, K.; Inanaga, J.; Yamaguchi, M. Tetrahedron Lett. 1986, 27, 3889. https://doi.org/10.1016/S0040-4039(00)83907-6
  27. Molander, G. A.; Etter, J. B. J. Am. Chem. Soc. 1987, 109, 6556. https://doi.org/10.1021/ja00255a076
  28. Huang, X.; Xie, L.; Wu, H. Tetrahedron Lett. 1987, 28, 801. https://doi.org/10.1016/S0040-4039(01)80993-X
  29. Fustner, A. Synthesis 1989, 571.
  30. Fustner, A. Angew. Chem. Int. Ed. Engl. 1993, 32, 164. https://doi.org/10.1002/anie.199301641
  31. Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
  32. Mason, T. J.; Lorimer, J. P. Sonochemistry: Theory, Applications and Uses of Ultrasound in Chemistry; Ellis Horwood Limited: Chichester, 1988.
  33. Han, B. H.; Boudjouk, P. J. Org. Chem. 1982, 47, 5030. https://doi.org/10.1021/jo00146a044
  34. Nishiyama, T.; Woodhall, J. F.; Lawson, E. N.; Kitching, W. J. Org. Chem. 1989, 54, 2184.
  35. Lee, P. H.; Bang, K.; Lee, K.; Lee, C.-H.; Chang, S. Tetrahedron Lett. 2000, 41, 7521. https://doi.org/10.1016/S0040-4039(00)01290-9
  36. Lee, P. H.; Bang, K.; Ahn, H.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1385.
  37. Lee, P. H.; Seomoon, S.; Lee, K. Bull. Korean Chem. Soc. 2001, 22, 1380.
  38. Lee, P. H.; Lee, K.; Sung, S.-Y.; Chang, S. J. Org. Chem. 2001, 66, 8646. https://doi.org/10.1021/jo0105641
  39. Lee, P. H.; Lee, K.; Kim, S. Org. Lett. 2001, 3, 3205. https://doi.org/10.1021/ol016542i
  40. Lee, P. H.; Sung, S.-Y.; Lee, K. Org. Lett. 2001, 3, 3201. https://doi.org/10.1021/ol016532h
  41. Lee, P. H.; Lee, K.; Chang, S. Synth. Commun. 2001, 31, 3189. https://doi.org/10.1081/SCC-100105896
  42. Lee, P. H.; Ahn, H.; Lee, K.; Sung, S.-Y.; Kim, S. Tetrahedron Lett. 2001, 42, 37. https://doi.org/10.1016/S0040-4039(00)01872-4
  43. Lee, P. H.; Sung, S.-Y.; Lee, K.; Chang, S. Synlett 2002, 146.
  44. Lee, P. H.; Bang, K.; Lee, K.; Sung, S.-Y.; Chang, S. Synth. Commun. 2001, 31, 3781. https://doi.org/10.1081/SCC-100108228

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