ORGLIST: Re: conversion of Enol to Keto tautomer

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From: muralidhar pendyala (pendyala123$##$gmail.com)
Date: Sun May 21 2006 - 11:03:30 EDT

Dear All,

I have to prepare a monophosphate on a primary alcohol group in the presence
of two sec alcohols of a glycoside . I am doing with POCl3 and triethyl
phosphate at 0 C. Reaction is completing well. I am facing problems while
isolation of product. I tried different ways:
  (i) Removal of triethyl phosphate & POCl3 by toluene, dissolving in water
by adjusting pH to 11 with NaOH followed by treating aqueous solution with
activated Dowex resin. But in this way, we obtained salts & 40-60 % purity
by assay.
 (ii) Quenching with water & removal of triethyl phosphate by fractionating
with MDC followed by adjusting pH to 2 with 50 % NaOH. In this method, we
obtained very hygroscopic salt material with low yield.

Please help in this regard.

Thanking you

With regards
Pendyala


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