This project lab explored the applications of directed ortho metalation in organic synthesis.
From the Paper:
" In particular a piperidine based directing group 2, an amide, was obtained from o-toluyl chloride 1. The amide 2 was deprotonated at the ortho position with sec-BuLi and an electrophile, benzylaldehyde, was introduced. The introduction of the electrophile resulted in the addition of a benzyl alcohol group onto the deprotonated amide, resulting in the final product 3. The amide 2 was high in yield with 92.4% being recovered; however the final product 3 was low in yield with only 34.0% being recovered. The amide 2 was identified as such through spectral information obtained from IR, 1H NMR, and 13C NMR. The final product 3 was not produced as was determined through spectral information obtained from IR, and 1H NMR."
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