I tried to tosylation glycerol carbonate with sodium hydride base in THF solvent. but C=O bond in glycerol carbonate was broken. can you help me what is the reason of that? is it becauce of the time or temprature of rection or order of adding materials?
The use of NaH (strong base) may be the main reason which enolizes the ketone. I prefer to use cesium carbonate or sodium bicarbonate, or triethylamine instead. Try to do the reaction at 0 degrees or minus degree celsius. I hope this will help. For more reference: https://www.organic-chemistry.org/synthesis/O1S/sulfonates.shtm
thank you so much for your help. Is it possible that sodium hydride has reacted with water in THF instead of glycerol carbonate?
If you have a related article, please give me.
thanks
Yes, NaH reacts with water. Add base first and cooled down to zero degree followed by addition of TsCl or MsCl. Read this one: https://www.thieme-connect.de/media/synthesis/201517/supmat/sup_ss-2015-m0308-psp_10-1055_s-0034-1378867.pdf
hope this helps!
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