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Lukash Tatarka

Flash Column Chromatography Problem - nothing eluting

David Rosen  Follow
Pure hexane is a poor solvent and as lipophilic as you can get so. Try to dissolve your material before loading. Toluene is a better solvent but usually dont impact on Rf

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Caleb Brunson  Follow
Probably TLC was too concentrated, and it smeared up the plate under non equilibrating conditions. Like Babcock_Hall said: always flush with polar solvent like 100% EtOAc or 100% acetone or 10% MeOH/DCM to elute it or decomp off the column. Could be a solid and it precipitated at the baseline therfore not moving far. These are common problems. Try TLC again with dilute sample.

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BPS Glass  Follow
I am not sure what is going on.  One thing you could try is a step gradient with increasing percentages of diethyl ether, DCM, or some other solvent in the hexane, as opposed to moving immediately to the flushing step.

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Donald Propp  Follow
Quote from:
Probably TLC was too concentrated, and it smeared up the plate under non equilibrating conditions. Like Babcock_Hall said: always flush with polar solvent like 100% EtOAc or 100% acetone or 10% MeOH/DCM to elute it or decomp off the column. Could be a solid and it precipitated at the baseline therfore not moving far. These are common problems. Try TLC again with dilute sample.

The TLC didn't have a smeared appearance so this didn't cross my mind, but it's definitely ssomething to consider. It is a solid yeah, so your idea that it precipitated at the top of the column seemes likely. I flushed with ethyl acetate to recover everything thankfully. I'll try with a different solvent system.
It's strange that the literature procedure states the same solvent system. I wonder what I was doing differently, or if they misreported.

Thank you very much for the advice. If anyone else has any thoughts please let me know. I am still very concerned and want to make sure I can avoid this in future.

Edit: typo

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