ORGLIST: deprotection of the ethylene glycol protected 2, 4, 6-tricyanobenzyl aldehyde

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From: Ruisong Xu (rsxu$##$siu.edu)
Date: Tue Aug 23 2005 - 00:08:31 EDT


Hello, everyone,

Just wondering if anyone can help me to figure out how to deprotect the =
ethylene glycol protected 2,4,6-tricyanobenzyl aldehyde. Seems to be an =
easy reaction. However, I tried to use tosylic acid, HCl, AlCl3+ =
N,N-dimethyl aniline, or I2 with acetone to cleave it but none was =
successful. But the ethylene glycol protect 2,4,6-tribromobenzyl =
aldehyde can be deprotected pretty easily by tosylic acid in acetone. =
Please give me some advice if anyone ever had similar experience. Thanks =
a lot.

Ruisong Xu

Department of Chem. and Biochem.
Southern Illinois University at Carbondale
Carbondale, IL 62901


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