When I use Ph2SiHCl with InCl3 to selectively reduce the benzylic alcohol to methylene functional group without affecting the primary alcohol functional groups on the susbtrate, finally the procedure on JOC paper told that I should add TBAF 1.0M in THF finally and let it react in 80 oC for 1 more hours. However, what it turned out was that after the silica column, I found 10% impurity which was from the tetrabutylammonium salt? So could I know what is the good method to rid of this tetrabutylammonium salt? The only method was did the column again?
An Operationally Simple and Efficient Work-up Procedure for TBAF-mediated Desilylation; Application to Halichondrin Synthesis:
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2519602/
This question already been addressed. Follow that method to get rid of excessive TBAF and it's salt.
https://www.researchgate.net/post/Can_anyone_suggest_a_good_TBAF_work_up_that_does_not_drag_through_tetrabutylammonium_salts
Ammonium salts are polar and should be removed by column. Even at 100% ethylacetate, these ammonium salts tend to remain in the column...
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