[rleung]

Hi,

I am wondering whether or not this synthesis works.  The main part that I wasn't too sure about was the use of the Gilman reagent to act as a nucleophile in attacking the C of C=O.  I had never seen that done, but I made an educated guess that it might work since the Gilman reagent makes the carbon that it is attached to very nucleophilic.  

Thanks so much

Ryan

[movies]

You can't make that aryl lithium reagent because the protons on the nitrogen are more acidic than those on the aromatic ring (pKas of 27 and 37, respectively), so you would just quench your anion like when you try to make a Grignard reagent in the presence of an alcohol.