Facile Synthesis of Dendritic Benzyl Chlorides from Their Alcohols with Methanesulfonyl Chloride/$Et_3N$

덴드리틱 벤질 클로라이드의 효율적인 합성

  • Published : 2007.09.30

Abstract

A successful rapid synthesis of dendritic benzyl chlorides from dendritic benzyl alcohols using methanesulfonyl chloride/$Et_3N$ as activating agents was described. In this method, each dendritic benzyl chloride can be prepared in one pot: no isolation of intermediate mesylated dendrons is required. The key steps in the syntheses of dendritic benzyl chlorides were the mesylation of the hydroxymethyl group followed by the chlorination by in-situ generated triethylammonium chloride.

덴드리틱 벤질 알코올을 트리에틸아민과 메탄술포닐클로라이드와 반응시켜서, 덴드리틱 벤질 클로라이드의 효율적인 합성이 이루어졌다. 이 반응은 히드록시기의 메실화 반응과 염소화 반응의 2단계 반응으로 이루어지는데, 중간체의 분리없이 한 반응 용기내에서 반응이 진행되는 경제적인 방법이다.

Keywords

References

  1. (a) A. C. Grimsdale and K. Mullen, Angew. Chem. Int. Ed, 44, 5592 (2005) https://doi.org/10.1002/anie.200500805
  2. (b) D. A. Tomalia, Prog. Polym. Sci, 30, 294 (2005) https://doi.org/10.1016/j.progpolymsci.2005.01.007
  3. (a) D. A. Tomalia, H. Baker, J. Dewald, M. Hall, G. Kallos, S. Martin, J. Roeck, J. Ryder, and P. Smith, Polym. J., 17, 117 (1985) https://doi.org/10.1295/polymj.17.117
  4. (b) D. A. Tomalia, A. M. Naylor, and W. A. Goddard III, Angew. Chem., Int. Ed Engl., 29, 138 (1990) https://doi.org/10.1002/anie.199001381
  5. (a) C. J. Hawker and J. M. J. Frechet, J. Am. Chem. Soc., 112, 7638 (1990) https://doi.org/10.1021/ja00177a027
  6. (b) C. J. Hawker and J. M. J. Frechet, J. Chem. Soc., Chem. Commun, 1010 (1990)
  7. (c) S. M. Grayson and J. M. J. Frechet, Chem. Rev., 101, 3819 (2001) https://doi.org/10.1021/cr990116h
  8. (a) J. W. Lee and B. K. Kim, Bull. Korean Chem. Soc., 26, 658 (2005) https://doi.org/10.5012/bkcs.2005.26.4.658
  9. (b) J. W. Lee, B. K. Kim, and S. H. Jin, Bull. Korean Chem. Soc., 26, 715 (2005) https://doi.org/10.5012/bkcs.2005.26.5.715
  10. (c) J. W. Lee, B. K. Kim, and S. H. Jin, Bull. Korean Chem. Soc., 26, 833 (2005) https://doi.org/10.5012/bkcs.2005.26.5.833
  11. (d) J. W. Lee, B. K. Kim, J. H. Kim, W. S. Shin, and S. H. Jin, Bull. Korean Chem. Soc., 26, 1790 (2005) https://doi.org/10.5012/bkcs.2005.26.11.1790
  12. (e) J. W. Lee and B. K. Kim, Synthesis, 615 (2006)
  13. (f) J. W. Lee, J. H. Kim, B. K. Kim, W. S. Shin, and S. H. Jin, Tetrahedron, 62, 894 (2006) https://doi.org/10.1016/j.tet.2005.10.039
  14. (g) J. W. Lee, B. K. Kim, J. H. Kim, W. S. Shin, and S. H. Jin, J. Org. Chem, 71, 4988 (2006) https://doi.org/10.1021/jo0605905
  15. A. Nantalaksakul, R. R. Dasari, T.-S. Ahn, R. Al-Kaysi, C. J. Bardeen, and S. Thayumanavan, Org. Lett; 8, 2981 (2006) https://doi.org/10.1021/ol0608956
  16. B. Forier and W. Dehaen, Tetrahedron, 55, 9829 (1999) https://doi.org/10.1016/S0040-4020(99)00566-9
  17. A. Basso, B. Evans, N. Pegg, and M. Bradley, Chem. Commun., 697 (2001)
  18. F. C. Whitmore, F. A. Karnatz, and A. H. Popkin, J. Am. Chem. Soc., 60, 2540 (1938) https://doi.org/10.1021/ja01277a076
  19. (a) V. S. K. Balagurusarnv, G. Ungar, V. Percec, and G. Johansson, J. Am. Chem. Soc., 119, 1539 (1997) https://doi.org/10.1021/ja963295i
  20. (b) V. Percec, W.-D. Cho, P. E. Mosier, G. Ungar, and D. J. P. Yeardley. J. Am. Chem. Soc., 120, 11061 (1998) https://doi.org/10.1021/ja9819007
  21. (c) V. Percec, W.-D. Cho, G. Ungar, and D. J. P. Yeardley, J. Am. Chem. Soc., 123, 1302 (2001) https://doi.org/10.1021/ja0037771
  22. (d) V. Percec, C. M. Mitchell, W.-D. Cho, S. Uchida, M. Glodde, G. Ungar, X. Zeng, Y. Liu, V. S. K. Balagurusarny, and P. A. Heiney, J. Am. Chem. Soc., 126, 6078 (2004) https://doi.org/10.1021/ja049846j
  23. (e) M. Tanaka, Y. Higuchi, N. Adachi, Y. Shibutani, S. A. Ahmed, S. Kado, M. Nakamura, and K. Kimura, Tetrahedron, 61, 8159 (2005) https://doi.org/10.1016/j.tet.2005.06.037
  24. (f) N. Yamazaki, I. Washio, Y. Shibasaki, and M. Ueda, Org. Lett., 8, 2321 (2006) https://doi.org/10.1021/ol0605880
  25. (a) Y. Sawada, H. Kayakiri, Y. Abe, T. Mizutani, N. Inamura, M. Asano, C. Hatori, I. Aramori, T. Oku, and H. Tanaka, J. Med Chem., 47, 2853 (2004) https://doi.org/10.1021/jm030468n
  26. (b) K. Tanaka, M. Katsurada, F. Ohno, Y. Shiga, M. Oda, M. Miyagi, J. Takehara, and K. Okano, J. Org. Chem., 65, 432 (2000) https://doi.org/10.1021/jo991271z
  27. (c) F. Mazzini, A. Mandoli, P. Salvadori, T. Netscher, and T. Rosenau, Eur. J. Org. Chem., 4864 (2004)