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Topic: TLC and nonvolatile reaction solvents  (Read 3011 times)

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Offline Babcock_Hall

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TLC and nonvolatile reaction solvents
« on: January 19, 2016, 05:46:25 PM »
Suppose we use DMF, DMSO, or something similar as a reaction solvent.  If we hope to follow the reaction by TLC, is there a convenient way to remove the solvent?  If not, is there a way to deal with its presence.  If it has greater polarity than the TLC developing solvent, it is surely going to be a problem, unless I am missing something.

Offline kriggy

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Re: TLC and nonvolatile reaction solvents
« Reply #1 on: January 20, 2016, 01:39:25 AM »
You could use hair dryer to evaporate the solvent, also, I never spot the reaction mixture but I dilute it with something volatile (methanol, acetone) then spot it and then dry. No problem for me. But my reaction are done in more volatile solvents

Offline TheUnassuming

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Re: TLC and nonvolatile reaction solvents
« Reply #2 on: January 20, 2016, 07:58:23 AM »
For the high boiling solvents I usually put TLC plates under high-vac for a few minutes after spotting.  Not a perfect fix depending on the reaction, but generally works well enough to see whats going on. 
When in doubt, avoid the Stille coupling.

Offline Dan

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Re: TLC and nonvolatile reaction solvents
« Reply #3 on: January 21, 2016, 01:53:51 AM »
I also put the plate under high vac. I don't like heating the plate in case it causes degradation.

For DMF and DMSO I sometimes do a mini workup: partition one drop of the reaction mixture between ~100 uL brine and ~100 uL of ether or EtOAc and TLC the organic layer. 
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Offline Babcock_Hall

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Re: TLC and nonvolatile reaction solvents
« Reply #4 on: January 21, 2016, 09:10:53 AM »
Great suggestions.  Thank you.

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