Problem_Set_4_Answer_Key - Organic Chemistry c3444y Problem...

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EtO OEt O O Br Br CO 2 Et EtO 2 C H 3 O + , Δ CO 2 H 1. Propose a synthesis to accomplish the following transformation. 2. O NMe 2 1. SOCl 2 2. HNMe 2 , Et 3 N NC CN O OMe O ? OMe O MeO O 1. NaOMe MeOH 2. H 3 O + As always, if you work backwards from the prod- uct (must recognize this as the product of a Dieckmann), the relation- ship to the starting material becomes much clearer. H 3 O + OH O HO O MeOH, H + Dieckmann CO 2 Me CO 2 Me O CO 2 Me 2. H 3 O + 1. NaOMe, MeOH 3. This is another Dieckmann Cond. We have two possible sites of enolization, but only one will lead to a product that has an enolizable proton between the carbonyls. O MeO 2 C The other possible product is:
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