ORGLIST:Cyanohydrin formation and dehydration

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From: Omar Khan (drkhan_99$##$yahoo.com)
Date: Wed Oct 02 2002 - 09:26:24 EDT


Hi everybody

Here is a problem. I am trying to form cyanohydrin and
then dehydrated to unsaturated nitrile of
6-keto-N-benzyl-isoquinuclidine. I tried
diethylaluminiumcyanide, and KCN methods for
cyanohydrin formation. Seems both worked well. But the
problem is I could get very little yield (say 5-10%)
of the dehydrated product when tried with pyridine and
POCL3, that was left at 80C for 3 hours. And seems to
get some polymers which is difficult to seperate.

Any suggestion would be gratefully acknowledged.

Faruk

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