Hey all - I'm just starting out with chemistry, and I have tried to think this one through a bit ... can anyone offer any help?
I am trying to completely alkylate an aniline with methylbromoacetate, but I must do so with several phenolic OH's elsewhere in my molecule. Phenolic OH's are quite acidic, and I do not want to alkylate them. On the other hand, I have a relatively small amount of material, and don't want a costly protection-deprotection round.
I was thinking to protect the phenols in-situ with 0.95 equivalents of t-butyldimethylsilyl chloride ... Is this what the wise one would do? And if so, what conditions would be sufficient to deprotect TBDMS protected phenols that I could do in the work-up (to deprotect with confidence)?
Similar N-alkylations generally proceed in the 12-16 hour ball-park in acetonitrile reflux, or dmf 100 degrees.
Any advice & principled reasoning would be awesome since I am just starting out!