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ChemInform Abstract: Synthesis of Esters from Silyl Ethers and Acyl Chlorides: Catalysis by Quaternary Ammonium Chlorides.

✍ Scribed by S. BRANDAENGE; H. LEIJONMARCK; T. MINASSIE


Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis


Synthesis of Esters from Silyl Ethers and Acyl Chlorides: Catalysis by Quaternary Ammonium Chlorides. -Quaternary ammonium chlorides are more efficient than other ammonium halides as catalysts in the title reaction. Acetyl chloride reacts faster than benzoyl chloride and trimethylsilyl ethers react faster than silyl ethers with bulkier Si-substituents, e.g. (I). The regioselectivity in monoacylation of (I) increases continuously from 96.6% after 1 h to 99.3% after 7 h, but during the second acylation to give (V) there is some decrease in isomeric purity (from 99.3 to 98.2%) that can be raised to 98.9% with tin(IV) chloride as catalyst instead of Bu4NCl.


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