[sjb]

I would guess that's the problem. See e.g. http://dx.doi.org/10.1039/b008270h though (but this is a tertiary amide, and so has no proton on the nitrogen to abstract).

S

[Squirmy]

I would guess that's the problem. See e.g. http://dx.doi.org/10.1039/b008270h though (but this is a tertiary amide, and so has no proton on the nitrogen to abstract).

S

that's not a fair example...looks like the point of the article is that molecule doesn't behave at all like an amide. The nitrogen is forced into a pyramidal geometry, so the lone pair doesn't overlap with the pi bond. Essentially it behaves as an amine/ketone.

[sjb]

That was (more or less) my point. You can get amides to undergo Wittig chemistry, but only if they don't really act like (typical) amides.

[alphahydroxy]

I like your idea alphahydroxy

Why thank you!

but rather than Glycine just start from aminoethanol.

Fair enough, I'd imagine there is very little it in, price-wise, so using a later intermediate would def be preferable!

Also where would you get the 1,2,-dichloroacetone from? A quick search in Aldrich shows the closest analogue as 1,1-dichloroacetyl chloride.

As others have said, I think this should be relatively straightforward from the acyl chloride - I didn't actually check the availabilty of the ketone

I am also not so sure the imine would from in preference to a simple alkylation but it may be feasable. Also the compound would probably cyclise easily and all you'd need is a simple reduction. Mmmmm it all depends on the imine formation but a good short synthesis...

Yeah, not sure bout that - I think there is a sporting chance that the imine will be the preferred pathway though - worth giving it a shot like!

Also, just had a quick look and, unless my computer is playing up (which is possible...), the final product  is NOT a known compound - something I find rather surprising...!

Perhaps there is some inherent instability with the chloro-ether fragment that prevents its isolation...?

[sjb]

Also, just had a quick look and, unless my computer is playing up (which is possible...), the final product  is NOT a known compound - something I find rather surprising...!

Perhaps there is some inherent instability with the chloro-ether fragment that prevents its isolation...?

Just because it looks simple, doesn't mean it's been made .

Perhaps the problem is something like this - similar intermediates to the oxonium ion are postulated in acetal hydrolysis if memory serves?

Once you have the aminochloroaldehyde who knows what may happen...

[lutesium]

What do you want it for lutesium or is it purely theoretical?

have you come up with any disconnections leading to for example cheap starting materials.

Have a look at alanine and amino ethanol...

Of course its purely theoretical!!!

[aldoxime_amine]

Another wacky idea, don't know how feasible it is mind.

I know you can form 3-chloropyridine from pyrrole and dichlorocarbene, so what about 4-methyloxazole treated in the same way then reduced? I appreciate there's not the aromatic stabilisation here?

I would like to agree with you.

[eeeaa]

from morpholine

[russellm72]

In reply to
 
Of course its purely theoretical!!!

Can you explain this statement lutesium.

I'm in the business of making money from Chemistry and was wondering why you were posting this compound.

One doesn't need a stubborn statement all I meant was if you actually wanted to make it people might of put more effort in to their thoughts and help you out.

Regards

R.

[alphahydroxy]

I don't think this statement was meant to cause offence! Though, as it wan't me who said it, it's possible that it was...

When you say that you're "in the business of making money from chemistry", what do you mean by that, out of interest? Do you run a company? Don't mean to be too nosy, I am just interested!

The molecule in question looks to me like a precursor to phenmetrazine, though I'm sure there are other potential applications.

[eeeaa]

Phenmetrazin synthesis:

started from PPA http://en.wikipedia.org/wiki/Phenylpropanolamine

[lutesium]

Phenmetrazin synthesis:

started from PPA http://en.wikipedia.org/wiki/Phenylpropanolamine

But I don't want this synthesis I want a -Cl atom attached en lieu of Phenyl ring attachment

[gfunk]

Haha, nah.  I'm perfectly happy to be wrong, and still a student myself.  But using the knowledge I've gained, I don't see much wrong with "wittig-ing" an amide.  Is there something about the wittig reaction and amide that would create an incompatibility?  Is the amide just acidic enough to destroy the ylide?

If I remember correctly, the resonance structures of the amide reduces the electrophilicity and thus reactivity of amide carbonyl carbons, rendering them quite ineffective for various nucleophilic attacks, such as with Wittig reagents.

In the paper cited, the geometry does not allow for the resonance structures to form (p-orbitals not co-planar) and thus the Wittig reaction can occur.

[lutesium]

In reply to
 
Of course its purely theoretical!!!

Can you explain this statement lutesium.

I'm in the business of making money from Chemistry and was wondering why you were posting this compound.

One doesn't need a stubborn statement all I meant was if you actually wanted to make it people might of put more effort in to their thoughts and help you out.

Regards

R.

I don't think that you've understood me correctly!!! Its my writing style!!! I always put three exclamation marks after everything I write!!! Call it obsession but not a stubborn statement ok???

though I'm sure there are other potential applications.

Yes you're right!!! I'm working over a vasodilator so I need this compound!!! But everything is on theory right now!!! Thanx to all for your constructive thoughts!!!


Lutesium...

[gfunk]

Haha, nah.  I'm perfectly happy to be wrong, and still a student myself.  But using the knowledge I've gained, I don't see much wrong with "wittig-ing" an amide.  Is there something about the wittig reaction and amide that would create an incompatibility?  Is the amide just acidic enough to destroy the ylide?

Poking around, I found the Tebbe Olefination which is essentially "Wittig-ing" an amide .

http://www.organic-chemistry.org/namedreactions/tebbe-olefination.shtm