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

A new efficient and rapid experimental method and product isolation procedure as well as easy recyclable reaction media is expected to contribute to the development of a green strategy for the synthesis of furan diol from d-glucal. We determine the best conditions of reaction, minimizing the toxicity and finding an environmentally more acceptable process, using [Bmim][MSO4]/InCl3·3H2O as a new solvent system under extremely mild conditions, providing high yields with a dramatic enhancement of reaction rate.

[1]  S. Kirsch.  Syntheses of polysubstituted furans: recent developments. , 2006, Organic & biomolecular chemistry.

[2]  C. Song,et al.  Ionic liquids as powerful media in scandium triflate catalysed Diels–Alder reactions: significant rate acceleration, selectivity improvement and easy recycling of catalyst , 2001 .

[3]  Robin D. Rogers,et al.  Ionic liquids are not always green: hydrolysis of 1-butyl-3-methylimidazolium hexafluorophosphate , 2003 .

[4]  Y. Fall,et al.  The furan approach to oxacycles. Part 5: Synthesis of a chiral butenolide, building block towards biologically interesting natural products , 2005 .

[5]  P. Wasserscheid,et al.  Ionic Liquids-New "Solutions" for Transition Metal Catalysis. , 2000, Angewandte Chemie.

[6]  Robin D. Rogers,et al.  Ionic liquids as green solvents : progress and prospects , 2003 .

[7]  D. Horton,et al.  Synthesis and reactions of unsaturated sugars , 1966 .

[8]  J. Yadav,et al.  Montmorillonite KSF clay as novel and recyclable heterogeneous solid acid for the conversion of d-glycals into furan diol , 2005 .

[9]  J. Canosa,et al.  Properties of ionic liquid HMIMPF6 with carbonates, ketones and alkyl acetates , 2006 .

[10]  J. Tojo,et al.  Temperature Dependence of Physical Properties of Ionic Liquid 1,3-Dimethylimidazolium Methyl Sulfate , 2006 .

[11]  Jeffrey B. Sperry,et al.  Furans, thiophenes and related heterocycles in drug discovery. , 2005, Current opinion in drug discovery & development.

[12]  X. She,et al.  Efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives in the ionic liquid. , 2005, The Journal of organic chemistry.

[13]  R. Sheldon.  Catalytic reactions in ionic liquids. , 2001, Chemical communications.

[14]  A. Perlin,et al.  Catalysis by mercuric ion of reactions of glycals with water , 1975 .

[15]  B. Ranu,et al.  Ionic liquid as reagent. A green procedure for the regioselective conversion of epoxides to vicinal-halohydrins using [AcMIm]X under catalyst- and solvent-free conditions. , 2005, The Journal of organic chemistry.

[16]  Balasubramanian,et al.  A facile synthesis of a chiral furan diol from glycals catalyzed by indium trichloride , 2000, The Journal of organic chemistry.

[17]  M. Hayashi,et al.  Metal-catalyzed transformation of D-glucal to optically active furan diol , 1999 .

[18]  R. P. Swatloski,et al.  Efficient, halide free synthesis of new, low cost ionic liquids: 1,3-dialkylimidazolium salts containing methyl- and ethyl-sulfate anions , 2002 .

[19]  S. Rani,et al.  Protic acid (HClO4 supported on silica gel)-mediated synthesis of 2,3-unsaturated-O-glucosides and a chiral furan diol from 2,3-glycals. , 2004, The Journal of organic chemistry.