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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: dielsalder33 on October 28, 2007, 03:30:33 PM

Title: Allylation using CH2=CH-CH2-Sn(n-Bu)3
Post by: dielsalder33 on October 28, 2007, 03:30:33 PM

Hi,
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.
Ben

Title: Re: Allylation using CH2=CH-CH2-Sn(n-Bu)3
Post by: Shaun on November 21, 2007, 02:21:46 PM

Does the compound you're trying to make have any polar functional groups?  You can always do a column starting with hexanes or hexanes:ether 10:1, flush out the organotin compounds, and then ramp up in polarity to elute your product.

If the compound you're making is also very nonpolar then it could be a bit tougher.

Maybe you could try using closer to 1.0 equivs instead of 1.3.  Three n-butyl groups per molecule means 27 aliphatic hydrogens.  That's a lot of "grease".  Things may not be as bad as they appear.