By Bensyloxymethyl do you mean like a PMB group?
So my problem is scale up. Doing something on 1 gram is all fine and dandy. You just run a column. But I do not have the capability, or the desire honestly, to run a large column. It is really expensive with all the solvent you use.
In this particular case is would be 11-dodecyn-1-ol to protected 11-dodecyn-1-ol. Then Sonogashira (Pyrrolidine, CuI, a vinyl bromide, Pd(Ph3)4). Then I want to attempt a Zn/Cu reduction to give the Z diene. Deprotection and TEMPO oxidation gives the aldehyde.
That is pretty much it. I was also thinking if a dimethyl acetal or the glycol acetal of 11-dodecynal would survive those conditions. I may just have to do it to see.
Anyone have experience with these types of acetals?