Re: ORGLIST: Everybody Digest, Vol 30, Issue 5

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From: Anand Pandey (anand.pandey$##$alembic.co.in)
Date: Thu Jan 11 2007 - 00:46:20 EST


Hello Jay,
Do the reaction in pyridine only and monitor the reaction with GLC/TLC. HPLC
leads degradation of products. It will be clean reaction in pridine only.
Regards
ANAND
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Subject: Everybody Digest, Vol 30, Issue 5

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> 1. Re: chlorosulfation (Andrew Lund)
> 2. Re: chlorosulfation (Jay)
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> ----------------------------------------------------------------------
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> Message: 1
> Date: Tue, 9 Jan 2007 08:20:15 -0600
> From: Andrew Lund <android109$##$hotmail.com>
> Subject: Re: ORGLIST: chlorosulfation
> To: Jay <hi_buddy03$##$yahoo.com>, google <everybody$##$orglist.net>
> Message-ID: <BAY123-W24FDBF31C6F95A13F63778CB30$##$phx.gbl>
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>
> Is it possible that what's happening is that the sulfuryl chloride is
chlorinating the alcohol and then under the HPLC conditions this is
hydrolysing back to the starting alcohol? Sulfuryl chloride is very reactive
and I'd expect it toi react immediately with the alcohol. Is the
chlorosulfonate the final target or is it simply an activated intermediate
where perhaps mesylate might be a better choice...?
> Andy
>
>
>
>
> ________________________________
> > Date: Mon, 8 Jan 2007 14:29:34 -0800
> > From: hi_buddy03$##$yahoo.com
> > To: everybody$##$orglist.net
> > Subject: ORGLIST: chlorosulfation
> >
> > Hello all,
> > I am trying to perform a chlorosulfation reaction as an intermediate
step.
> > The reaction is as follows:
> > Ar-CH2OH + SO2Cl2 --------> Ar-CH2OSO2Cl
> > (3 mol) (3.6mol)
> > Toluene as solvent and pyridine as a base.
> > I am monitoring this reaction on HPLC but I cannot see anything other
than the starting material peak.
> > I thought SO2Cl2 being very reactive would give the product easily.
> > I need some feedback on as to whether the method that I am using for
synthesis has flaws or the reaction monitoring method is incorrect?
> > If anybody has a new approach to this synthesis should also be fine.
> > Thanks,
> > Jay
> > __________________________________________________
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> Message: 2
> Date: Wed, 10 Jan 2007 05:43:49 -0800 (PST)
> From: Jay <hi_buddy03$##$yahoo.com>
> Subject: Re: ORGLIST: chlorosulfation
> To: Andrew Lund <android109$##$hotmail.com>, google
> <everybody$##$orglist.net>
> Message-ID: <976089.59126.qm$##$web90605.mail.mud.yahoo.com>
> Content-Type: text/plain; charset="iso-8859-1"
>
> I am using THF as the mobile phase for HPLC so I wonder if the compound is
still getting hydrolyzed. Also, if there is a better way to monitor this
reaction please let me know.
> I am using this reaction to incorporate the SO2 group so the final
strucutre after this reaction would be Ar-CH2-O-SO2Cl
> The next step I want to try is to substitute the Cl group.
>
> Regards,
> Jay
>
> Andrew Lund <android109$##$hotmail.com> wrote:
>
> Is it possible that what's happening is that the sulfuryl chloride is
chlorinating the alcohol and then under the HPLC conditions this is
hydrolysing back to the starting alcohol? Sulfuryl chloride is very reactive
and I'd expect it toi react immediately with the alcohol. Is the
chlorosulfonate the final target or is it simply an activated intermediate
where perhaps mesylate might be a better choice...?
> Andy
>
>
>
>
> ________________________________
> > Date: Mon, 8 Jan 2007 14:29:34 -0800
> > From: hi_buddy03$##$yahoo.com
> > To: everybody$##$orglist.net
> > Subject: ORGLIST: chlorosulfation
> >
> > Hello all,
> > I am trying to perform a chlorosulfation reaction as an intermediate
step.
> > The reaction is as follows:
> > Ar-CH2OH + SO2Cl2 --------> Ar-CH2OSO2Cl
> > (3 mol) (3.6mol)
> > Toluene as solvent and pyridine as a base.
> > I am monitoring this reaction on HPLC but I cannot see anything other
than the starting material peak.
> > I thought SO2Cl2 being very reactive would give the product easily.
> > I need some feedback on as to whether the method that I am using for
synthesis has flaws or the reaction monitoring method is incorrect?
> > If anybody has a new approach to this synthesis should also be fine.
> > Thanks,
> > Jay
> > __________________________________________________
> > Do You Yahoo!?
> > Tired of spam? Yahoo! Mail has the best spam protection around
> > http://mail.yahoo.com
>
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