Non-destructive real-time reaction monitoring in solid phase synthesis by near-infrared reflectance spectroscopy—esterification of a resin-bound alcohol

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Jonathan Hammond, Anthony C. Moffat, Roger D. Jee and Barrie Kellam


Abstract

Near-infrared (NIR) reflectance spectroscopy has been used to monitor the chemical inter-conversion of resin-bound functional groups. Measurements required no sample preparation and were made directly through the bottom of the glass reaction vessel. The time–concentration profile of the esterification of a resin-bound alcohol by acetic anhydride in a toluene medium is demonstrated.


References

  1. G. C. Look, C. P. Homes, J. P. Chinn and M. A. Gallop, J. Org. Chem., 1994, 59, 7588 CrossRef CAS.
  2. C. R. Johnson and B. Zhang, Tetrahedron Lett., 1995, 36(51), 9253 CrossRef CAS.
  3. R. C. Anderson, M. A. Jarema, M. J. Shapiro, J. P. Stokes and M. Ziliox, J. Org. Chem., 1995, 60, 2650 CrossRef CAS.
  4. M. J. Shapiro, G. Kumaravel, R. C. Petter and R. Beveridge, Tetrahedron Lett., 1996, 37(27), 4671 CrossRef CAS.
  5. H. Moon, N. E. Schore and M. J. Kurth, J. Org. Chem., 1992, 57, 6088 CrossRef CAS.
  6. J. R. Hauske and P. Dorff, Tetrahedron Lett., 1995, 36(10), 1589 CrossRef CAS.
  7. B. Yan, G. Kumaravel, H. Anjaria, A. Wu, R. C. Petter, C. F. Jewell, Jr. and J. R. Wareing, J. Org. Chem., 1995, 60, 5736 CrossRef CAS.
  8. T. Y. Chan, R. Chen, M. J. Sofia, B. C. Smith and D. Glennon, Tetrahedron Lett., 1997, 38(16), 2821 CrossRef CAS.
  9. T. Norris and P. K. Aldridge, Analyst, 1996, 121, 1003 RSC.
  10. P. Brush, NIR News, 1994, 5(5), 14 Search PubMed.
  11. H. R. Bjoersvik, Appl. Spectrosc., 1996, 50(12), 1541 CAS.
  12. J. Mijovic, S. Andjelic and J. M. Kenny, Polym. Adv. Technol., 1995, 7, 1 CrossRef.
  13. C. Gwosdz, M. S. Francis and A. Bickel, Process Control & Quality, 1992, 4, 31 Search PubMed.
  14. H. W. Siesler, NIR News, 1995, 6(1), 3 Search PubMed.
  15. J. Ryttersgaard, B. Due Larsen, A. Holm, D. H. Christensen and O. Faurskov Nielsen, Spectrochim. Acta, Part A, 1997, 53, 91 CrossRef.
  16. Practical NIR Spectroscopy with Applications in Food and Beverage Analysis, ed. B. G. Osborne, T. Fearn and P. H. Hindle, Longman Ltd., Harlow, UK, 1993, p. 23 Search PubMed.
  17. B. Yan, J. B. Fell and G. Kumaravel, J. Org. Chem., 1996, 61(21), 7467 CrossRef CAS.
  18. R. A. Alberty and R. J. Silbey, in Physical Chemistry, Wiley, New York, 1st edn., 1992, p. 623 Search PubMed.
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