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 Chapter 21: Ester Enolates
Ch 21 contents
Acylation of Ketones
acylation of a ketone enolate
Reaction type : Nucleophilic Acyl Substitution

Summary

Acylation using diethyl carbonate
Acylation using an ester

 
  • As an example, consider the reaction of acetone with diethyl carbonate, which gives ethyl acetoacetate:
acylation of acetone with diethyl carbonate

acylation of acetone with diethyl carbonate

Try to identify the enolate portion and the carbonyl portion in the different representations
QUESTION

The intramolecular variation of this reaction is also possible when forming the favourable 5- or 6- membered rings, giving a cyclic 1,3-diketone product:

Intramolecular variation
an intramolecular ketone acylation
Related Reactions
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© Dr. Ian Hunt, Department of Chemistry, University of Calgary