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selective trimethylsilylation of hydroxy group in presence of amine

selective trimethylsilylation of hydroxy group in presence of amine - Organic Chemistry Forum

selective trimethylsilylation of hydroxy group in presence of amine - Organic Chemistry Forum


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Old 02-25-2004, 09:59 PM
Glenn
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Default 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.

Thanks
Glenn
g.mcenroe(remove)@comcast.net (remove the (remove) to email me.
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amine , group , hydroxy , presence , selective , trimethylsilylation


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