I knew that organotin compounds are quite stable to aqueous conditions. However, performing a small-scale allylation of an aldehyde using 1.3 eq CH2=CH-CH2-Sn(n-Bu)3 led to so much (by mass and H-NMR) crude product containing organotin compounds, that I was really surprised. Is there a way to get rid of this material prior to column chromatography? I performed a workup using ether extraction and NaHCO3 washing.
I would be very thankful for ideas.