Has anyone observed the formation of dichlormethane-triethylamine salt, while performing the purification in silica column with DCM:methanol:triethylamine (95:4:1) system as mobile phase ?
If yes how can you remove it from the polar compound (Rf = 0.3 at 20% MeOH:DCM: a drop of triethylamine )?
DCM should not form any salt with TEA. The salt formation, if at all, may be because of some other components, or may be the silica is acidic. Have you tried alkaline treatment for silica (treating silica with sodium carbonate solution) before packing the column? It would also ease purification of the polar compound (if it is basic).
There is a risk that your DCM contains some HCl, which can form a salts.
I think it is highly unlikely that the DCM used for column chromatography would contain HCl. In fact, presence of HCl in such commonly used solvents would be a serious issue from safety perspectives!
To check it shake 10 mL of H2O with 100 or 500 mL of DCM, at the end check the pH of water phase.
So you can't do it. Maybe ask the corresponding author of the paper for more data.
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