Hi, so I have a compound which contains both OH and tertiary amine. Basically I am hoping to homologate the OH to a methoxy group by a Williamson ether synthesis, The problem is that this would also alkylate the amine, producing ammonium cations. Naturally I would prefer to avoid this
I attached a schematic with the proposed synthesis. If anyone would be willing to share what the right protective group mighty be here, and how the are added and removed again. I would be very grateful to know.
Cheers.
Ps: Suppose you want to go the other way around, and cleave the methoxy into a OH group. Could you apply the same procedure, where instead you use HBr to cleave the ether? (again by protecting the amine?