Re: ORGLIST: borohydride reduction

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From: support$##$cussyn.com
Date: Sat Nov 27 2004 - 15:27:20 EST


Dr.Mehta,

When reducing methyl esters to alcohols I have repeatedly had
very good results using NaBH4 in 1:1 Dioxane:H2O (~0.1 M rxn),
however the molarity of the reaction may be adjusted depending
on the molcecule and the scale of the reaction

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 extraction
if possible.

Good luck

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