selective trimethylsilylation of hydroxy group in presence of amine
I want to protect the hydroxyl group of an amino alcohol with
trimethylsilyl for easy removal at the next step. Following a
literature procedure that did not characterize the product I used 1
equivalent bis(trimethylsilyl)acetamide. After aqueous workup,
extraction with ether the nmr of my product showed 2 TMS groups by
integration. I expected aqueous workup which literature procedure
didn't do to deprotect any TMS-amine leaving the TMS ether intact. I
may going to try trimethylsilyl imidazole next. It is supposed to
selectively protect alcohols in presence of amine. If anyone has some
other suggestions please let me know.
g.mcenroe(remove)@comcast.net (remove the (remove) to email me.
Paul J. Franklin(moderator - sci.chem.organic.synthesis) [Only registered users see links. ]
Georgia State University <[Only registered users see links. ].edu>