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Author Topic: Ligand synthesis (Urgent!)  (Read 1027 times)

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kentso1234

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Ligand synthesis (Urgent!)
« on: December 18, 2012, 03:40:43 AM »

My name is Ken and I am a postgraduate student. Now I have a problem in synthesizing a ligand and I hope someone can help me overcome it.

The ligand structure: 
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discodermolide

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Re: Ligand synthesis (Urgent!)
« Reply #1 on: December 18, 2012, 03:43:11 AM »

Urgent, urgent, what have you tried, what is the problem?
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curiouscat

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Re: Ligand synthesis (Urgent!)
« Reply #2 on: December 18, 2012, 03:49:53 AM »

One idea is to perhaps mix Borane, Ethylene Glycol, and Ammonia(aq.) a handful of Transition Metals and pass through an Urey-Miller apparatus? The yields might be low though.

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kentso1234

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Re: Ligand synthesis (Urgent!)
« Reply #3 on: December 18, 2012, 03:50:59 AM »

Urgent, urgent, what have you tried, what is the problem?


I have problem in synthesizing such ligand since I am not a organic chemist. I can't find the relevant reference  or procedures in synthesizing it in SciFinder.
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kentso1234

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Re: Ligand synthesis (Urgent!)
« Reply #4 on: December 18, 2012, 03:53:06 AM »

One idea is to perhaps mix Borane, Ethylene Glycol, and Ammonia(aq.) a handful of Transition Metals and pass through an Urey-Miller apparatus? The yields might be low though.



Thanks for your comment. But i wonder is there any simplified method in doing this? Because I only treat this as one of the intermediates in my reaction so I don't want spend too much time in synthesizing it. :)
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curiouscat

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Re: Ligand synthesis (Urgent!)
« Reply #5 on: December 18, 2012, 03:54:34 AM »


Thanks for your comment. But i wonder is there any simplified method in doing this? Because I only treat this as one of the intermediates in my reaction so I don't want spend too much time in synthesizing it. :)

Yes, you are right. I'd probably not try this way either.  :(
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discodermolide

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Re: Ligand synthesis (Urgent!)
« Reply #6 on: December 18, 2012, 03:59:44 AM »

Actually curious, your way might not be too bad, worth a go?

To the OP, find the procedures for pinacol borane preps. and adapt them. Pinacolborane is commercially available.

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Dan

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Re: Ligand synthesis (Urgent!)
« Reply #7 on: December 18, 2012, 04:31:50 AM »

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curiouscat

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Re: Ligand synthesis (Urgent!)
« Reply #8 on: December 18, 2012, 06:02:55 AM »

Actually curious, your way might not be too bad, worth a go?

Always been a fan of The Natural Selection School Of Organic Synthesis myself.
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kentso1234

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Re: Ligand synthesis (Urgent!)
« Reply #9 on: December 18, 2012, 06:52:50 PM »

This is a known compound.

J. Chem. Soc., Dalton Trans., 1972, 1123-1129

I know, but I can't find this paper on Internet even in library storage.
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camptzak

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Re: Ligand synthesis (Urgent!)
« Reply #10 on: December 18, 2012, 07:15:46 PM »

what about reacting borane with basic ethylene glycol in a 2:1 ethylene glycol to borane ratio. Then react with sodium amide and neutralize. would that work?

B2H6 + 2 Na+ C2H5O2  :rarrow: 2 BO4C4H8

BO4C4H8 + Na+NH2

my thinking is that the sodium amide would attack the boron complex kicking off one of the oxygen's and forming an alcohol, and the neutralization would completely remove ethylene glycol...
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Dan

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Re: Ligand synthesis (Urgent!)
« Reply #11 on: December 18, 2012, 08:55:53 PM »

This is a known compound.

J. Chem. Soc., Dalton Trans., 1972, 1123-1129

I know, but I can't find this paper on Internet even in library storage.

I posted the link (blue text). Click it. If you don't have online access and your library can't get it, you will have to buy the article.
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