β-KETO ESTERS FROM REACTION OF ETHYL DIAZOACETATE WITH KETONES
- 1 June 1964
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 42 (6) , 1333-1340
- https://doi.org/10.1139/v64-205
Abstract
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.Keywords
This publication has 9 references indexed in Scilit:
- The Acid-catalyzed Reaction of Diazomethane with Some α,β-Unsaturated KetonesJournal of the American Chemical Society, 1962
- The Reaction of Ketones with DiazomethaneJournal of the American Chemical Society, 1960
- ETHYL DIAZOACETATEOrganic Syntheses, 1956
- Salt Effects on the Indicator Acidity Function, H01Journal of the American Chemical Society, 1954
- Reactions of diazoacetates and diazoketones. I. Reaction of ethyl diazoacetate with cyclohexanone and with acetoneThe Journal of Organic Chemistry, 1953
- Synthese von β‐Ketonsäureestern mittels Diazoessigester. IIEuropean Journal of Inorganic Chemistry, 1909
- Synthese von β‐Ketonsäureestern mittels DiazoessigesterEuropean Journal of Inorganic Chemistry, 1907
- Ueber Condensationsproducte cyclischer Ketone (III)European Journal of Inorganic Chemistry, 1897
- Synthese von Ketonsäureäthern aus Aldehyden und DiazoessigätherEuropean Journal of Inorganic Chemistry, 1885