β-KETO ESTERS FROM REACTION OF ETHYL DIAZOACETATE WITH KETONES

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<jats:p> The Lewis acid catalyzed reaction of diazoacetic ester with ketones has been extended. Convenient conditions have been found for the preparation of some pure β-keto esters in fair to good yields by reaction of ethyl diazoacetate with ketones in the presence of boron trifluoride at −40° to −70°. The reaction is apparently general since cyclopentanone, cyclohexanone, and acetophenone gave nearly pure β-keto esters in 44%, 79%, and 38% yields, respectively, based on diazoacetic ester. In the case of acetophenone the phenyl group migrated. Acetone gave 78% of a mixture of β-keto ester and glycidic ester. </jats:p>

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