|
Ester Condensations
(Carey, Chap. 21) |
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| Reaction | Product | Notes | ||||||||||||||||||||||||||||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 
| Claisen condensation. Must be able to form beta- ketoester enolate anion intermediate 
| Beta-ketoester cleavage; reverse of ester condensation 
| Mixed ester condensation; R'' must have no alpha H's 
| Mixed condensation- ketone with ester; beta-diketone product 
| Dieckmann cyclization. Intramolecular ester condensation; 5 or 6 memb. rings only 
| Intramolecular ketone with ester condensation; 5 or 6 memb. rings only 
| Malonate ester alkylation R' can be 1o or 2o 
| Decarboxylation of beta- carbonyl acid. "Malonic ester synthesis" Syn of substituted acids 
| Acetoacetic ester alkylation R' can be 1o or 2o 
| Decarboxylation of beta- carbonyl acid. "Acetoacetic ester synthesis" Syn of substituted ketones 
| Michael reaction 
| Pre-formed ester enolate R' must be 1o only 
| Pre-formed ester enolate Mixed condensation with alde. or ketone | ||||||||||||||||||||||||