Efficient and rapid experimental procedure for the synthesis of furan diol from d-glucal using ionic liquid

Tetrahedron Letters

Volumn 48, Issue 45, 2007, Pages 7926-7929

  Teijeira, Marta ^a   Fall, Yagamare ^a   Santamarta, Francisco ^a   Tojo, Emilia ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

Diols; Furans; Green chemistry; Ionic liquids; Solvent effects

Indexed keywords

FURAN; GLUCONATE CALCIUM; IONIC LIQUID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ISOLATION PROCEDURE; REACTION ANALYSIS; RECYCLING; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 35148876506     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.070     Document Type: Article

References (24)

1. Kirsch S.F. Org. Biomol. Chem. 4 (2006) 2076
2. Sperry J.B., and Wright D.L. Curr. Opin. Drug Discov. Devel. 8 (2005) 723
3. Horton D., and Tsuchiya T. Chemistry and Industry (London, United Kingdom) 48 (1966) 2011
4. Albano E., Horton D., and Tsuchiya T. Carbohydr. Res. 2 (1966) 349
5. Gonzalez F., Lesage S., and Perlin A.S. Carbohydr. Res. 42 (1975) 267
6. Hayashi M., Kawabata H., and Yamada K. Chem. Commun. 11 (1999) 965-966
7. Sobhana Babu B., and Balasubramanian K.K. J. Org. Chem. 65 (2000) 4198
8. Agarwal A., Rani S., and Vankar Y.D. J. Org. Chem. 69 (2004) 6137
9. Yadav J.S., Reddy B.V.S., and Madhavi A.V. J. Mol. Catal. A: Chem. 226 (2005) 213
10. Rogers, R. D.; Seddon, K. R. Ionic Liquids As Green Solvents: Progress and Prospects: Washington DC, USA, 2003.
11. Welton T. Chem. Rev. 99 (1999) 2071
12. Wasserscheid P., and Keim W. Angew. Chem., Int. Ed. 39 (2000) 3772
13. Song C.E., Shim W.H., Roh E.J., Leea S.G., and Choi J.H. Chem. Commun. 12 (2001) 1122
14. Li Y., Zhang J., Wang W., Miao Q., She X., and Pan X. J. Org. Chem. 70 (2005) 3285
15. Sheldon R. Chem. Commun. 23 (2001) 2399
16. Ranu B.C., and Banerjee S. J. Org. Chem. 70 (2005) 4517
17. Teijeira M., Lois Suarez P., Gomez G., Teran C., and Fall Y. Tetrahedron Lett. 46 (2005) 5889
18. Pereiro A.B., Santamarta F., Tojo E., Rodriguez A., and Tojo J. J. Chem. Eng. Data 51 (2006) 952
19. Pereiro A.B., Tojo E., Rodriguez A., Canosa J., and Tojo J. J. Chem. Thermodyn. 38 (2006) 651
20. 4, concentrated and purified by column chromatography. Yields ranged from 73% to 78%.
21. tBuOMe or THF and drying under vacuum. The combined organic extracts were concentrated to afford d-glucal.
22. tBuOMe or THF. The combined organic extracts were concentrated and purified by column chromatography. Yields ranged from 5% to 80%. The ionic liquid was recycled by drying under vacuum.
23. Swatloski R.P., Holbrey J.D., and Rogers R.D. Green Chem. 5 (2003) 361
24. Holbrey J.D., Reichert W.M., Swatloski R.P., Broker G.A., Pitner W.R., Seddon K.R., and Rogers R.D. Green Chem. 4 (2002) 407