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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: charty on January 23, 2007, 10:59:37 AM

Title: tin removal from reduction reactions
Post by: charty on January 23, 2007, 10:59:37 AM

I am going to do a reduction of an aromatic nitro compound using tin chloride and HCl.
I want to remove the tin from the reaction without using strongly basic conditions or H2S, does anybody have any other methods for doing this?

Title: Re: tin removal from reduction reactions
Post by: AWK on January 23, 2007, 12:38:54 PM

Can you use ammonia?

Title: Re: tin removal from reduction reactions
Post by: charty on January 23, 2007, 12:57:00 PM

no. I have a chlorine in the molecule that is likely to displace.

Title: Re: tin removal from reduction reactions
Post by: Ψ×Ψ on January 23, 2007, 08:41:20 PM

Well...I've never done it with nitro compounds, but I usually just extract with CH₂Cl₂ and water (often with a bit of HCl in there).  If you get a nasty emulsion, filter and then try to extract again.  What solvent are you using for the reaction?

Title: Re: tin removal from reduction reactions
Post by: russellm72 on June 21, 2007, 05:17:59 AM

Hi,

I have done a few tin reductions before and they go quite cleanly. If I remember I did the reaction in ethanol/c.HCl and when complete diluted with water and extracted into ether. Clearly without knowing more about the solubility of your product this may not be suitable.

Do you have to use dissolving metal reduction? Whats wrong with a good old ammonium formate transfer hydrog. I did one the other day with a Ar-Cl present with no problems. Is this also out of the question due to other reducible functional groups.

R.

Title: Re: tin removal from reduction reactions
Post by: sa1chavez on August 06, 2007, 08:59:53 PM

try a sat KF (aq) solution wash. or you can try stiring the reaction with KF/Celite (1"1 mix by weight 200g of each and 200ml of water. stir for  hour and concentrate down with acetonitril)  sorry i dont have the exact refrence but search roush its in an org. lett paper that refrences a chem lett paper.

cant use if you have silane protecting groups