Re: ORGLIST: nitrile to carboxylate ester

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From: Jacob Zabicky (zabicky$##$bgumail.bgu.ac.il)
Date: Mon Jan 31 2005 - 23:13:35 EST


Hello Omar,

Perhaps using a Pd catalyst as in the following paper and similar
publications will do the trick.

Natalia V. Kaminskaia, Ilia A. Guzei† and Nenad M. Kostic, J. Chem.
Soc., Dalton Trans., 1998, 3879–3885

All the best,

Jacob
Prof. Jacob Zabicky
Institutes for Applied Researcfh
Ben-Gurion University of the Negev
P. O. Box 653
Beer-Sheva, 84105
Israel
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On Feb 1, 2005, at 0:02, Omar Khan wrote:

> Hi everybody,
>
> I would be pleased if someone is so kind to help me
> out with the reaction I am running at present. It is
> the methanolysis of nitrile to get methyl carboxylate
> ester of a steroid.
>
> Because of the Mettox rearrangement problem at steroid
> hydroxy/methoxy group when the reaction is run at
> around 0oC or higher the reaction is run at -20oC to
> -15oC, but still I am not getting any satisfactory
> product.
>
> can anybody suggest me of any alternative mild
> reaction condition avoidong alkali/acid hydrolysis of
> nitrile to get carboxylate?
>
> Thank you very much
>
> Omar Faruk Khan
> College of Pharmacy
> Florida A & M University
> Tallahassee, FL 32307
>
>
>
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