Re: ORGLIST:problem of reduction

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From: S.BARTOLI$##$soton.ac.uk
Date: Thu Jun 03 2004 - 11:10:39 EDT


Why don't you treat it with a 1M HCl aqueous solution (pour your reaction
mixture into the HCl solution under vigorous stirring after quenching it with
EtOAc)and then filter the solid, which should be your alcohol? That's what I
used to do.
Hope it helps. If you have any questions let me know.
Cheers,

Sandra

Scrive stephanie <roulle.stephanie$##$wanadoo.fr>:

> Hello everybody,
> I have a problem with a reduction. I want to reduce an ester to an
> alcohol with LiAlH4 / THF. The reaction is perfect but my problem is the
> treatment. The alcohol obtained is very cristalline and insoluble in all
> solvant. It precipitate when I treat my reaction.
> I tried to hydrolyse with HCl and extract with dichloromethane and there
> is precipitation. I also tried to hydrolyse with Na2SO4 with water and
> also precipitation and I cannot separate Na2SO4 and the obtained
> alcohol. I tried at last to hydrolyse with THF/water, there is also
> precipitation, I evaporate the THF and put isopropanol and filtrate. The
> problem is that my yield is over 100% because I have also aluminium
> hydroxyde and I cannot separate them of my product.
> Can anybody help me please ???
>
>
> stephanie
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