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Topic: tin removal from reduction reactions  (Read 9825 times)

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Offline charty

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tin removal from reduction reactions
« 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?

Offline AWK

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Re: tin removal from reduction reactions
« Reply #1 on: January 23, 2007, 12:38:54 PM »
Can you use ammonia?
AWK

Offline charty

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Re: tin removal from reduction reactions
« Reply #2 on: January 23, 2007, 12:57:00 PM »
no. I have a chlorine in the molecule that is likely to displace.

Offline Ψ×Ψ

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Re: tin removal from reduction reactions
« Reply #3 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?

Offline russellm72

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Re: tin removal from reduction reactions
« Reply #4 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.

Offline sa1chavez

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Re: tin removal from reduction reactions
« Reply #5 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

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