Subject: Re: CCL:converting a -CH3 to a C(CH3)3

From: Richard Wood <rlw28(at)cornell.edu>
Date: Wed, 16 Jun 2004 07:24:53 -0600

Hi all

I didn't get a satisfactory answer, so I'll try again. 

I would like to replace an -O-C(CH3)2-COOH group with an 
-O-C(C(CH3)3))2-COOH group.  I know it can be done, because the group 
that is on the molecule now replaced a methyl group. In other words, the 
molecule I have is a derivative of a previously made one.  I can't say 
more than this about my molecule.  Those of you that work for a company 
will understand this.

Richard

Richard Wood wrote:

> Hi all
>
> This a synthesis question.  I've done some computations and converted 
> a methyl group into a t-butyl group with no problem.
>
> My question is how can a methyl group be converted synthetically into 
> a t-butyl group?  If anyone out there knows how, including reagents,
> conditions etc. please let me know.
>
> Thank you in advance,
> Richard
>

-- 
Richard L. Wood, Ph. D.
Computational Chemist
SynVax, Inc.
N. Logan, UT 84341

---

From: "David F. Green" <dfgreen[at]ai.mit.edu>
Date: Wed, 16 Jun 2004 06:42:42 -0400 (EDT)

This depends entirely on the details of the molecule, and the current
synthetic scheme being used for it.  In some cases, the reagent initially
containing the methyl is also available (or easily synthesized) with a
t-butyl, and the alternate synthesis may be straightforward (although
differences in reactivity can still lead to difficulties).  However, in
other cases the synthetic stragety must be changed to make the
substitution.  In any case, it's not at all straightforward to convert
a methyl to a t-butyl in the context of a larger molecule, and thus the
conversion should be done early on in the synthetic process.

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On Tue, 15 Jun 2004, Richard Wood wrote:

> Hi all
> 
> This a synthesis question.  I've done some computations and converted a 
> methyl group into a t-butyl group with no problem.
> 
> My question is how can a methyl group be converted synthetically into a 
> t-butyl group?  If anyone out there knows how, including reagents,
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