Since I assume this is some undergrad lab example, why not do a click reaction? Benzyl azide+propargyl alcohol in the presence of catalytic Bromotris(triphenylphosphine)copper(I). I chose that Cu(I)/ligand because it supposedly makes CuAAC go under ambient conditions. Its fairly cheap, and only needs in a few mol %.
If you're a grad student and inventing new click chemistry is the goal... well isn't figuring that out your job?