Synthesis of Ethyl Di T-Butyl Acetate and its Enolate
Cook, Gary L.
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An ester enolate is formed from the reaction between an ester of the form RR'HCCOOR" and a very strong base. Since the hydrogen to the carbonyl carbon is acidic, the base, usually a lithium dialkyl amide, can remove it to form a resonance stabilized carbanion, called an ester enolate. The possibilities of the use of ester enolates in organic synthesis is presently being researched by Dr. M. W. Rathke and his students at Michigan State University. The enolates are usually stable only at dry ice temperatures. At higher temperatures the enolate can undergo condensation reactions with the ester, for example, the Claisen condensation to form B -keto esters. Another reaction which can take place under the right conditions is an elimination; the formation of a ketene. The ketene is usually very reactive and reacts further with the ester or enolate to form a number of condensation products, an interesting situation arises when the enolate of an ester of the highly hindered di- t-butyl acetic acid is prepared. The t-butyl groups prevent many condensation products from forming due to steric hinderance. The preparation of this ester, and its enolate is the topic of this thesis.