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Topic: Will this work? - Organic Synthesis  (Read 3041 times)

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Offline maverick1996

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Will this work? - Organic Synthesis
« on: April 04, 2016, 03:58:54 AM »
Hey guys!!

I am just wondering whether this method would work? And if there is a better way of doing it?

I have attached both the question and my scheme

Thank you


Offline AWK

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Re: Will this work? - Organic Synthesis
« Reply #1 on: April 04, 2016, 04:07:41 AM »
Wrong position of double bond in last two lines.
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Offline maverick1996

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Re: Will this work? - Organic Synthesis
« Reply #2 on: April 04, 2016, 04:15:21 AM »
Thank you

Offline Alwin Kristen

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Re: Will this work? - Organic Synthesis
« Reply #3 on: April 04, 2016, 06:22:37 AM »
How would you know that your methyl iodide reacts with lactaldehyde and not with NaOH? Could another base be better? Some big and just strong enought to remove proton from hydroxyl group?
Let us learn to dream, we then might find the truth. - F. A. Kekulé

Offline AWK

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Re: Will this work? - Organic Synthesis
« Reply #4 on: April 04, 2016, 06:48:18 AM »
Good remark. Aldehyde also reacts itself in presence of NaOH. Though conditions are theoretically anhydrous. I used CaH2 or molecular sieves for drying DMSO.
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Offline kriggy

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Re: Will this work? - Organic Synthesis
« Reply #5 on: April 04, 2016, 09:32:58 AM »
You could probably get rid of the hydroxy group by use of HI in one step.

Im wondering, if acetone derivative could be used in this, like forming enol-ether and then arylate it with bromobenzene in presence of some metal catalyst

Offline clarkstill

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Re: Will this work? - Organic Synthesis
« Reply #6 on: April 04, 2016, 11:07:46 AM »
Any way you could think of using an epoxide?

Offline discodermolide

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Re: Will this work? - Organic Synthesis
« Reply #7 on: April 04, 2016, 12:45:04 PM »
What about a metal catalysed aryl-vinyl cross coupling?
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Offline maverick1996

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Re: Will this work? - Organic Synthesis
« Reply #8 on: April 06, 2016, 02:58:24 AM »
Thank you all for your input, I'm a first year so I'm just going by the reactions that I've already seen but I'll give it a shot with the ways that you have suggested :)

And about using NaOH - thank you

Offline subro

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Re: Will this work? - Organic Synthesis
« Reply #9 on: April 10, 2016, 06:17:30 AM »
Any way you could think of using an epoxide?

Yeah, I was going to post this.

Offline phth

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Re: Will this work? - Organic Synthesis
« Reply #10 on: April 10, 2016, 08:35:22 PM »
What about a metal catalysed aryl-vinyl cross coupling?
+1 this transformation can be done in 1 step. Ni(II) Hiyama coupling.  Ni is better than Pd.

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