Problem

You are working in a medicinal chemistry lab and your supervisor has asked you to synthesize derivatives of the

anticoagulant Warfarin to investigate the effect of these derivatives on the potency of the drug. Specifically, they

are interested in the effect of adding an alkyl chain on one of the aromatic rings of the Warfarin backbone.

Your supervisor suggests that you should start the project by looking up how Warfarin can be synthesized then

modifying this synthesis to obtain the desired derivatives.

Questions

Please answer the questions to guide your approach to solving this problem.

Propose a racemic synthesis of Warfarin starting from simple starting materials $($benzaldehyde$,$ acetone,

ethyl malonate, and phenol$).$ You may use any other reagents required.

How could you start your research project of making derivatives of Warfarin? Which original starting mate$-$

rial $($benzaldehyde$,$ acetone, ethyl malonate, or phenol$)$ could you modify and how would you do that? How

would you expect to characterize your product $($what instrumentation would you use to prove you made an

alkyl derivative of Warfarin$)?$

Show each step in your proposed synthesis. After each step of the synthesis, how would you go about con$-$

firming that you made the product you think you made? Please describe the instrumentation you would use

and what key pieces of information $($ex: signals on a spectrum$)$ could help you determine that you obtained

the products.