Skip to main content
Log in

Facile conversion of alcohols to olefins by tosylation and subsequent SiO2-promoted β-elimination

  • Published:
Journal of Ocean University of China Aims and scope Submit manuscript

Abstract

A convenient and effective procedure was developed for the conversion of alcohol to olefin by tosylation and subsequent β-elimination promoted by silica gel in this study. Treatment of the alcohols with p-toluenesulfonyl chloride in pyridine at 0°C affords tosylates which undergo β-elimination with silica gel in dichloromethane or chloroform at room temperature, yielding olefins with high productivity.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Dang, Q., B. S. Brown, and M. D. Erion, 2000. Effcient synthesis of purine analogues: an FeCl3-SiO2-promoted cyclization reaction of 4,5-diaminopyrimidines with aldehydes leading to 6, 8, 9-trisubstituted purines. Tetrahedron Lett., 41: 6 559–6 562.

    Google Scholar 

  • Kametani, T., T. Katoh., M. Tsubuki, and T. Honda, 1986. Stereochemistry and reactions of presilphiperfolanol: a branch point marker in triquinane sesquiterpene biogenesis. J. Am. Chem. Soc., 108: 7 055–7 060.

    Article  Google Scholar 

  • Kametani, T., M. Tsubuki, and H. Nemoto, 1980. Total synthesis of steroid hormones. Efficient stereocontrolled synthesis of 17-methoxy-6-oxo-D-homo-18-nor-5β-androsta-2, 13, 15, 17-tetraene. J. Org. Chem., 45: 4 391–4 398.

    Google Scholar 

  • Katsuyama, I., K. Funabiki, M. Matsui, H. Muramatsu, and K. Shibata, 1996. An effective synthesis of trifluoromethyl-substituted 1,4-dihydropyridines with phosphorus oxychloride/pyridine adsorbed on silica gel. Tetrahedron Lett., 24(37): 4 177–4 178.

    Google Scholar 

  • Niiyama, K., T. Yoshixumi, H. Takahashi, and A. Naya, 2002. A convenient synthetic method of a 5,7-diarylcyclopenteno-[1,2-b]pyridine-6-carboxylate: A key intermediate for potent endothelin receptor antagonists. Bioorg. Med. Chem., 10: 3 437–3 444.

    Article  Google Scholar 

  • Nishiguchi, T., N. Machida, and E. Yamamoto, 1987. Dehydration of alcohols catalyzed by copper (II) sulfate adsorbed on silica gel. Tetrahedron Lett., 28(39): 4 565–4 568.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Li Yingxia.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ruan, X., Song, G., Zhang, Y. et al. Facile conversion of alcohols to olefins by tosylation and subsequent SiO2-promoted β-elimination. J Ocean Univ. China 6, 196–198 (2007). https://doi.org/10.1007/s11802-007-0196-1

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11802-007-0196-1

Key words

Navigation