ORGLIST: ester hydrolysis

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From: Luis Fernando Garcia Alles (luis.garciaalles$##$ibc.unibe.ch)
Date: Wed Sep 27 2000 - 08:53:35 EDT


        Dear people,
        I'm trying to hydrolyze a methyl ester in a molecule which contains also a
phosphoenol function:

                                                        MeOOC-CH2-C(=CH2)-OPO3R2)

        I've tried to do it under standard conditions, NaOH/MeOH and NaOHaq,
without too much success. At best I've obtained the product contaminated
with others coming from side reactions (specially phosphoenol degradation).
I've tried also to perform the hydrolysis by enzymatic means, using a
lipase, without any good result. One of the last possibilities I might use
it's to hydrolyse it under acidic conditions:HCl saturated, but I'm
wondering about the stability of the phosphoenol group.
        Does anybody know of any procedure which might work under mild conditions??.
        Thank you very much for any answer.
        Bye-bye.
=====================================
Luis Fernando García Alles, Ph.D.
Departement für Chemie und Biochemie
Universität Bern
Freiestrasse 3
CH-3012 Bern, Schweiz
Tel. ++41 (0)31/631 37 92
Fax ++41 (0)31/631 33 83
E-mail :garcia$##$ibc.unibe.ch
=====================================

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