Example Ketone TM

This strategy offers a useful way to functionalize the commercially available ethyl acetoacetate. If it is followed with another a-alkylation and decarboxylation (acetoacetic ester synthesis), the final product will be an acetone molecule with alkyl groups added to both sides. 

Ethyl Acetoacetate as a Versatile Starting Material EXAMPLE KETONE TM 

Synthesize the following TM using readily available starting materials and reagents. The synthesis must involve the formation of a new C-C bond. 

Once again, there are several possible syntheses of this compound. One possibility is an FGl to an alcohol. This alcohol can then be disconnected in two different places and prepared by a Grignard reaction with either an aldehyde or an epoxide. While the epoxide disconnection may have a slight advantage by breaking the TM into more nearly equal pieces, both routes involve readily available starting materials and represent acceptable syntheses. Another good 

Three possible syntheses are presented for the given TM, each of which forms a new C-C bond as required, via Grignard or enolate reactions. 

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