Re: ORGLIST:problem of reduction

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From: support$##$cussyn.com
Date: Thu Jun 03 2004 - 18:44:48 EDT


Stephanie,

You may try an alternative reduction. When reducing methyl
esters to alcohols I have repeatedly had very good results
using NaBH4 in 1:1 Dioxane:H2O (0.1 M rxn). Dissolve your
ester in dioxane and then slowly add an equivalent volume of
water . If your ester begins to crash out of solution, add
enough additional dioxane to get a homogenous solution. Then
cautiously add 3-4 eq NaBH4 portionwise. Complete reduction
can be achieved within 1-12 hours at 25 C depending on the
molecule. Standard acidic workup follows and the resulting
boric acid should be water soluble. If your compound is as
insoluble as you claim, you may very well be able to simply
isolate by filtration.

Good luck

Brad
Senior Scientist-Chemist
Manager of Scientific Operations
Custom Synthesis Services
support$##$cussyn.com
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