Re: ORGLIST: Reformatsky reaction

Date view Thread view Subject view Author view Attachment view

From: Gary Breton (gbreton$##$berry.edu)
Date: Thu Jan 18 2001 - 09:26:40 EST


Ms. Joshi,

You may be interested in considering conducting the reaction under a solvent
mixture of water/THF as a Barbier-type reaction (where the organozinc
intermediate is generated in situ). Look up the following paper:

Li, Chao-Jun Tetrahedron 1996, 52, 5643 (and references therein).

I also think that I have seen some more recent advances in this type of
chemistry.

These aqueous reactions generally afford good yields of product and are
quite convenient to run.

Good luck!

Gary W. Breton
Department of Chemistry
Berry College
PO Box 495016
Mount Berry, GA 30149


> From: "priya joshi" <joshipgk$##$hotmail.com>
> Date: Tue, 16 Jan 2001 12:03:52
> To: Multiple recipients of list orglist <orglist$##$dq.fct.unl.pt>
> Subject: ORGLIST: Reformatsky reaction
>
>
> Hello
>
> I am Ms. Priya Joshi from Department of Chemistry, University of Pune,
> India.
>
> I am having some trouble while doing Reformatsky reaction on
> 5-benzofurancarboxaldehyde-7-methoxy-2-(3,4-methylenedioxyphenyl. This
> benzaldehyde does not dissolve in ether or benzene except in THF. Hence
> reaction was done in THF by reacting this benzaldehyde with organozinc
> reagent formed by the reaction of Zn(activated) and ethyl bromoacetate.
> Starting compound was recovered even after 3-4 h of refulx (under N2
> atmosphere).
>
> It would be great help if some one could possibly tell where I went wrong.
>
> Thanks in Advance.
>
> Priya Joshi
> _________________________________________________________________________
> Get Your Private, Free E-mail from MSN Hotmail at http://www.hotmail.com.
>
> __________________
>
> ORGLIST - Organic Chemistry Mailing List
> Website / Archive / FAQ: http://www.orglist.net/
> List coordinator: Joao Aires de Sousa (jas$##$mail.fct.unl.pt)
>

__________________

ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ: http://www.orglist.net/
List coordinator: Joao Aires de Sousa (jas$##$mail.fct.unl.pt)




Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Fri Sep 19 2003 - 12:16:27 EDT