Anyone has suggestion(s) on how to easily and efficiently remove excess silyl protected alcohols from a reaction mixture. Flash column is not helping and I sometime have to leave it under high vac for like 2 days before I can hope to have remove bits of it. Also, my desire compound has an ester, and tbs protected alcohol functionalities.
Any ideas are very well appreciated.
Thank you!!
It is not clear what is the reaction you are performing, silylating an alcohol or other reaction. Further, you didn't mention what are the silyl group impurities, is it from the TBS reaction?
Anyway your product appears to be quite non-polar with "tbs protected alcohols" i.e. multiple TBS groups. This is likely to be very difficult to purify by column, the product may be eluting out with pure hexane similar to the impurities.
The easiest way will be to push forward where you can make the product more polar to separate off the silyl impurities. There are too little details to be more specific...
Thank you for the reply #Eugene Yang.
To be more specific of the reaction, I first protected and alcohol with TBS. then the TBS-protected alcohol was used in a slight excess in a metal mediated coupling reaction with a trichloroethyl benzyl ester. My issue is that I am not able to remove the remaining(unreacted) tbs-protected alcohol from the reaction mixture. Thank you!
Without knowing the polarities for sure, it is difficult, but I think your TBS-protected alcohol starting material and coupled product are too non-polar to be separated easily.
You could consider using the ester in excess instead or deprotect the TBS groups to separate the coupled and uncoupled alcohols.
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