After seeking for references, most of the solvents for Dess-Martin is DCM, but my compound has a poor solubility in DCM. Because my compound is acid-sensitive, I prefer not to use IBX to oxidize my compound to aldehyde. I am wandering if DMP in DMF would produce side product or oxidize my compound to carboxylic acid? Thanks for help.
I checked one of the seminal papers for the possible solvents :
This an extract of J. Am. Chem. Soc. 1991, 113, 7277-7287
"The experimental procedure for oxidation by triacetoxyperiodinane
13 is very simple. Preparation for reaction simply involves
dissolving 13 in the appropriate anhydrous solvent (chloroform,
methylene chloride, acetonitrile, etc.) and adding the substrate."
Acetonitrile is rather polar and may work for your compound ?
A mixture DCM/DMSO was used in J. Org. Chem. 1997, 62, 9376-9378 for a modified protocol. I deduce that solvent mixtures may help.
Dear Shuo-Lin Weng please see the attached short article entitled "2-Iodoxybenzoic Acid (IBX) and Dess-Martin Periodinane (DMP)". Suitable solvents listed in this article are dichloromethane (DCM), DMSO, and pyridine. I would suggest to use DCM even is you starting material is not very soluble in this solvent. Changes are that it dissolves as the reaction proceeds. Of course you can also just try THF in a small-scale test reaction. Good luck!
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