Metal salt catalyzed process to oxazolines and subsequent formation of chloroketones
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United States of America Patent
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May 2, 2000
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app pub date -
Apr 16, 1999
filing date -
Apr 21, 1998
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Abstract
This invention relates to a process for the preparation of an .alpha.-chloroketone compound comprising the steps of (i) cyclizing an alkynyl amide to form a 5-methyleneoxazoline ##STR1## (ii) chlorinating the 5-methyleneoxazoline using trichlorolsocyanuric acid to produce a chlorinated oxazoline intermediate ##STR2## and (iii) hydrolyzing the chlorinated oxazoline intermediate with an aqueous acid to produce the desired monochloroketone ##STR3## wherein Z is alkyl or substituted alkyl, aryl or substituted aryl, heteroaryl or substituted heteroaryl or phenylene, R is a hydrogen atom or alkyl, and R.sup.1 and R.sup.2 are each independently an alkyl or substituted alkyl group, or R.sup.1 and R.sup.2 together with the carbon atom to which they are attached form a cyclic structure. Additionally, when R is a hydrogen atom, a dichloroketone can be conveniently formed through adjustment of reaction conditions.
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