ORGLIST: Re: Silyl Protection with HMDS (shrent)

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From: Robert J. Panetta (rj_panet$##$alcor.concordia.ca)
Date: Thu Jun 01 2006 - 12:27:10 EDT

Hi Shrent,
With HMDS, the typical catalyst is trimethylchlorosilane (TMCS). A typical
procedure involves mixing HMDS, TMCS and pyridine (ratios of 3:1:9, by volume)
and heating, typically between 60-100 degC, for between 60-120 minutes. The
mixture is sold by Sigma-Aldrich. I've also seem some analysts using
trifluoroacetic acid instead of TMCS. But the best solvent for silylation
reactions is pyridine.
Good luck!
Robert
>
> Message: 2
> Date: 1 Jun 2006 15:47:02 -0000
> From: "shrent" <shrent$##$rediffmail.com>
> Subject: ORGLIST: Silyl Protection with HMDS
> To: everybody$##$orglist.net
> Message-ID: <20060601154702.3999.qmail$##$webmail28.rediffmail.com>
> Content-Type: text/plain; charset="iso-8859-1"
>
> Hi !
>
> I'm trying silyl protection of l-Alanine with Hexamethyldisilazane (HMDS).
>
> i.e. making H2NCH(CH3)COOH to H2NCH(CH3)COOSi(CH3)3.
>
> How can I do this task ? Just mixing & reflux in acetonitrile or something
> else ? Adding base (TEA) is necessary ? 
>
>
>
>
> shrent
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-- 
Robert J. Panetta
Dept. Chemistry and Biochemistry
Concordia University
rj_panet$##$alcor.concordia.ca
(514)848-2424 ext. 7972
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