Problem_Set_8_solut - Chem 3580 Spring 2009 Problem Set 8 solutions 1(a Retrosynthesis O CH3 intramolecular aldol O O Decarboxylation CH3 O OH O O

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Chem 3580 - Spring 2009 Problem Set 8 - solutions 1. (a) Retrosynthesis O CH 3 O CH 3 O O CH 3 O O OH ! O CH 3 O O OEt ! " O O OEt O CH 3 + ! " intramolecular aldol Decarboxylation Hydrolysis Michael addition Ethyl acetoacetate Claisen CH 3 OC 2 H 5 O 2 Forward synthesis CH 3 O O 2 NaOEt (1 equiv) O O O Claisen CH 3 O CH 3 O O O O CH 3 O O O O Decarboxylation CH 3 O O NaOH (cat), H 2 O ! Intramolecular aldol O CH 3 Michael Addition O CH 3 O O O H Hydrolysis Ethyl acetate can be done in one step (H 3 O + , Heat) Na + H 3 O + H 3 O + ! (b) Retrosynthesis O O OH O O O O O O O + Br H 3 C O O CH 3 O O decarboxylation alkylation hydrolysis intra-molecular Claisen (Dieckmann) Forward synthesis H 3 C O O CH 3 O O 1. NaOEt (1 equiv) Intramolecular Claisen O O O CH 3 Br O O CH 3 O Alkylation of the enolate base hydrolysis (saponification) followed by mild acidic work-up O O H O ! Decarboxylation O 1. NaOH, H 2 O, ! 2. Dilute HCl, 25°C
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2. O O ! Br O EtO O O Ethyl acetoacetate !
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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Problem_Set_8_solut - Chem 3580 Spring 2009 Problem Set 8 solutions 1(a Retrosynthesis O CH3 intramolecular aldol O O Decarboxylation CH3 O OH O O

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