This issue was on discussion not long ago. It was proposed, that in case of polar products, probably the best is to try to crystallize it out from cold ether, where it has very low solubility. (Hopefully your product has still some.) You can also try chromatography of crude products using etheral solutions. If nothing works you could also think about selective complex formation with TPPO. There are lots of TPPO complexes known (see attachment below). Of course, selectivity should be checked first in this case.

TPPO recristalise in Diethylether it could be a way to remove a big part of it and then finish by a chromatography.

Good luck

I know that currently you just want to remove the PPh3O from your mixture, and I think that given advice above are good. But if it doesn't succeed, I have heard about supported PPh3, maybe it could help you... ?

Good luck

I would also recommend triturating the PPh3O out using diethyl ether as stated above. It works very well.   If there is any left in the reaction mixture, it should be removed in the chromatography (assuming this is necessary).

Hello Amith,

As you mentioned your product is polar and it comes in  25% MeOH in DCM.

So you can try crystalysation with 50% DCM in hexan solvent system, it may works.

Good luck.

Hi Amit, please let us know whether your desired product is acid or base sensitive? and whethet it contain any amino or carboxylic acid group?

Warm your mixture with ether and cool down in ice. Oxide might crystallized and your compound might remain in ether.

I was also having problems with PPh3O and my compound was eluting in 10% MeOH in DCM. I tried a buffer solvent system of 1% Et3N in 40% EtOAc in hexane and it worked great. I got my pure compound. Hope it works for you also. Good luck

Since you mention that your compound is very polar and dissolves only in MeOH+DCM, your job is very easy. Just triturate the solid with DCM in which TPPO is highly soluble!

TPPO is insoluble in hexane, add hexane to the RM make homogeneous cool the RM to 0- 5 ° C .THe UTPPO will ppt out.

Please read

http://en.wikipedia.org/wiki/Triphenylphosphine_oxide

r u able to do column chromatography with 25% MeOH/DCM in silica?

It depends upon the solubility of your compound and the scale at which it has to be purified. For small scale chromatography would be convenient whereas for large scale a solvent-extraction is efficient. If your compound is soluble in ether, triturate with this solvent. Your product will be in the solvent while TPPO will remain as sparingly soluble solid. If not, remove TPPO by triturating with DCM, which should leave your compound as undissolved solid.

hahaha

u most add NaSO3 (Sodium sulphite) and next add water. phenyles get in water

25% MeOH in silica? Unless its a modified silica, more than 5% MeOH starts dissolving silica too. You may have more trouble doing a column with this system.

first run the column with hex/EtOAc to remove the TPPO and then with DCM/MeOH to get your product.. I did the same for my compound

Add ZnCl2 to your compound in EtOH. TPPO will be precipitated in presence of ZnCl2 in EtOH. Then, you can filter it out.

Article Removal of Triphenylphosphine Oxide by Precipitation with Zi...

most relevant work

To remove Triphenyl phosphine oxide from my reaction mixture , concentrate the reaction mixture under vacuum & then treat residual mixture with n-hexane when triphenyl phosphine from the mixture. being less soluble will come out , then filter solid triphenyl phosphine