Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

A New Synthesis of a Chiral Ester Containing Phenylpyrimidine Rinf as Liquid Crystal Dopant

  • Published : 1995.06.20
Download PDF
⟨ Previous Next ⟩

Abstract

A new synthetic route to chiral liquid crystal dopant, 4-[2-(7S-methylnonanyl)oxy-5-pyrimidinyl]phenyl(2S,3S)-2-chloro-3-methylpentanoate (1), starting from 4-nitrophenylacetic acid is described. The key intermediate methylthiopyrimidine compound (8) has been synthesized from 4-nitrophenylacetic acid by Vilsmyer-Haack reaction followed by the formation of pyrimidine ring, and then converted to chiral ester (1) by the replacement of nitro group by (2S,3S)-2-chloro-3-methylpentanoic acid 2 through the formation of diazonium salt.

Keywords

References

  1. Ferroelectric Liquid Crystals Goodby, J. W.;Blinc, R.;Clark, N. A.;Lagerwall, S. T.;Osipov, M. A.;Pikin, S. A.;Sakurai, T.;Yoshino, K.;Zeks, B.
  2. Mol. Cryst. Liq. Cryst. v.206 Sakaigawa, A.;Tashiro, Y.;Aoki, Y.;Nohira, H.
  3. Mol. Cryst. Liq. Cryst. v.110 Goodby, J. W.;Leslie, T. M.
  4. Appl. Phys. Lett. v.36 Clark, N. A.;Lagerwall, S. T.
  5. Tetrahedron v.49 Wang, Q.;Fan, S. Y.;Wong, H. N. C.;Li, Z.;Fung, B. M.;Twieg, R. J.;Nguyen, H. T.
  6. Chem. Lett. Aoki, Y.;Nohira, H.
  7. Chem. Abstr. v.110 Bahr, C.;Heppke, G.;Loetzsch, D.;Duebal, H. R.;Guenter, D.;Hemmerling, W.;Mueller, I.;Wingen, R.
  8. Chem. Abstr. v.110 Terachi, T.;Takeno, S.;Sugita, S.
  9. J. Heterocycl. Chem. v.11 Coppola, G. M.;Hardtmann, G. E.;Huegi, B. S.
  10. J. Chem. Soc. Boarland, M. P. V.;McOmie, J. F. W.
  11. Org. Syn. Coll. v.2 Shildneck, P. R.;Windus, W.
  12. J. Org. Chem. v.50 Hine, J.;Hahn, S.;Miles, D. E.;Ahn, K.
  13. J. Org. Chem. v.51 Schurig, V.;Leyer, U.;Wistuba, D.
  14. Tetrahedron v.33 Wilen, S. H.;Collet, A.;Jacques, J.
  15. Org. Synth. Col. v.2 Ingersoll, A. W.
  16. Chem. Pharm. Bull. v.20 Kobayashi, M.;Koga, K.;Yamada, S. I.
  17. J. Am. Chem. Soc. v.55 Haller, H. L.;Schaffer, P. S.
  18. J. Am. Chem. Soc. v.61 Smith, L. E.;Haller, H. L.
  19. J. Chem. Soc. Cadogan, J. I. G.
  20. Synth. Col. v.2 Noyers, W. A.