Re: ORGLIST: Chemoselective reduction

Date view Thread view Subject view Author view Attachment view

From: Jacob Zabicky (zabicky$##$bgumail.bgu.ac.il)
Date: Tue Nov 23 2004 - 03:10:03 EST


Hello Andrea,

Perhaps this old reference will be of help:

Reduction of o-nitrobenzaldehyde to o-nitrobenzyl alcohol. Schenck,
Friedrich. Ber. (1934), 67B 1571. Chem. Abs. 28:59545

Abstract: In connection with the reduction of the keto group in the
isomeric 3-benzoyl-2-phenylcyclopropane-1-carboxylic esters without
altering the NO2 group or the cyclopropane ring, the stability of the
NO2 group toward metal (especially Al) alcoholates was investigated.
o-O2NC6H4CHO (10 g.), boiled with 1 g. Al and 50 cc. iso-PrOH, gave 9
g. o-O2NC6H4CH2OH, m. 74.

Other possible selective reducers can be NaBH4, and hydrogenation with
Pd/C catalysis at low pressure.

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
-------------------------------------
zabicky$##$bgumail.bgu.ac.il
Tel. +972-8-6461271
Fax. +972-8-6472969
-------------------------------------
Private: P. O. Box 12366
Beer-Sheva, 84863
Israel
Tel. +972-8-6496792

On Nov 21, 2004, at 23:16, Andrea Giordano wrote:

> Hello all,
>
> i would like to make a complete reduction of some nitroaryl
> aldehydes/ketones
> i have in hands without affecting an ester moiety also present in the
> molecule
> (and the nitro group). Anybody may suggest some good procedure? Would
> be more
> advisable to procede via reduction to the alcohol first and then go
> further?
> Should the nitro give problems, i may think of introducing it at the
> very
> end...
>
> Thanks for your help!
> Bye,
> --
> Andrea Giordano, PhD student
> Schultz group (Bioorganic chemistry of signaling molecules)
> http://www-db.embl-heidelberg.de/jss/emblGroups/g_162.html
> Gene Expression Program
> European Molecular Biology Laboratory
> Meyerhofstrasse, 1
> 69117 Heidelberg, Germany
> tel: 0049 6221 387 -498 (chem. lab) -264 (mol.bio. lab)
> fax: 0049 6221 387 206
>
>
>
>
> _______________________________________________
> ORGLIST - Organic Chemistry Mailing List
> Website / Archive / FAQ: http://www.orglist.net
> To post a message (TO EVERYBODY) send to everybody$##$orglist.net
> To unsubscribe, send to everybody-request$##$orglist.net the message:
> unsubscribe your_orglist_password your_address
> List coordinator: Joao Aires de Sousa (coordinator$##$orglist.net)
>


_______________________________________________
ORGLIST - Organic Chemistry Mailing List
Website / Archive / FAQ: http://www.orglist.net
To post a message (TO EVERYBODY) send to everybody$##$orglist.net
To unsubscribe, send to everybody-request$##$orglist.net the message: unsubscribe your_orglist_password your_address
List coordinator: Joao Aires de Sousa (coordinator$##$orglist.net)


Date view Thread view Subject view Author view Attachment view

This archive was generated by hypermail 2.1.4 : Tue Nov 23 2004 - 04:47:00 EST