[kentso1234]

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: 

[discodermolide]

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

[curiouscat]

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.

[kentso1234]

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.

[kentso1234]

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.

[curiouscat]

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. 

[discodermolide]

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.

[Dan]

This is a known compound.

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

[curiouscat]

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.

[kentso1234]

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.

[camptzak]

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  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...

[Dan]

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.