Novel 1,4-homofragmentation via an alpha-lactone |
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| Authors: | Godfrey Jollie D Fox Rita T Buono Frederic G Gougoutas Jack Z Malley Mary F |
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| Institution: | Department of Process Research and Development, Pharmaceutical Research Institute, Bristol-Myers Squibb, Post Office Box 4000, Princeton, New Jersey 08543-4000, USA. jollie.godfrey@bms.com |
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| Abstract: | Conversion of an alpha,alpha-dichloroester to the corresponding alpha-keto acid was unexpectedly complicated by a novel 1,4-homofragmentation. Investigation of the kinetics of this reaction revealed a mechanism involving an alpha-lactone intermediate, which can lead to both the desired alpha-keto acid and the 1,4-homofragmentation, with the product distribution being dependent upon reaction conditions. This information allowed development of a process that affords the alpha-keto acid exclusively and should be generally applicable to the preparation of alpha-keto acids from alpha,alpha-dichloroesters or acids. |
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