Dolbier HW Solutions 492 - NaOCH 2 CH 3 CH 3 CH 2 OH O COCH...

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( b ) Acylation of cyclohexanone with diethyl carbonate yields the same -keto ester formed in part ( a ). ( c ) The two most stable enol forms are those that involve the proton on the carbon fl anked by the two carbonyl groups. ( d ) Deprotonation of the -keto ester involves the acidic proton at the carbon fl anked by the two carbonyl groups ( e ) The methyl group is introduced by alkylation of the -keto ester. Saponi fi cation and decar- boxylation complete the synthesis. ( f ) The enolate ion of the -keto ester [see part ( d )] undergoes Michael addition to the carbon carbon double bond of acrolein. This reaction has been reported in the chemical literature and proceeds in 65
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Unformatted text preview: NaOCH 2 CH 3 CH 3 CH 2 OH O COCH 2 CH 3 O Ethyl (2-oxocyclohexane)-carboxylate H 2 C CHCH O Acrolein O O CH 2 CH 2 CH COOCH 2 CH 3 Michael adduct 1 NaOCH 2 CH 3 CH 3 Br 1. HO 2 , H 2 O O COCH 2 CH 3 O Ethyl (2-oxocyclohexane)-carboxylate O CH 3 COOCH 2 CH 3 Ethyl (1-methyl-2-oxocyclohexane)-carboxylate O CH 3 2-Methylcyclohexanone 2. H 1 3. heat O COCH 2 CH 3 O 2 O COCH 2 CH 3 O 2 O COCH 2 CH 3 O 2 O COCH 2 CH 3 O H O COCH 2 CH 3 O O COCH 2 CH 3 O H 1. NaOCH 2 CH 3 2. H 1 O Diethyl carbonate Cyclohexanone CH 3 CH 2 OCOCH 2 CH 3 O 1 Ethyl (2-oxocyclohexane)-carboxylate COCH 2 CH 3 O O 586 ESTER ENOLATES...
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