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Topic: Stuck on Claisen(?) reaction  (Read 2442 times)

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Offline jezzielee

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Stuck on Claisen(?) reaction
« on: June 19, 2014, 03:25:53 PM »
I have been trying to figure out this problem since last night but I have no clue where to even start, I think it is a claisen reaction problem though. Thanks!

Offline discodermolide

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Re: Stuck on Claisen(?) reaction
« Reply #1 on: June 19, 2014, 03:37:45 PM »
What do you know about the reactivity of the CH2 group of dimethyl malonate with a base and then an electrophile?
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Offline jezzielee

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Re: Stuck on Claisen(?) reaction
« Reply #2 on: June 19, 2014, 03:45:37 PM »
What do you know about the reactivity of the CH2 group of dimethyl malonate with a base and then an electrophile?

Well I think a carbanion forms and it is alkylated with an electrophile

Offline discodermolide

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Re: Stuck on Claisen(?) reaction
« Reply #3 on: June 19, 2014, 03:51:49 PM »
Ok do that then and see what you get when one of the bromines is displaced.
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Offline jezzielee

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Re: Stuck on Claisen(?) reaction
« Reply #4 on: June 19, 2014, 04:04:36 PM »
Ok do that then and see what you get when one of the bromines is displaced.

So far this is what I was able to figure out

Offline discodermolide

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Re: Stuck on Claisen(?) reaction
« Reply #5 on: June 19, 2014, 04:06:49 PM »
The first alkylation gives the diester you drew:
BrCCCCC([H])(C(OC)=O)C(OC)=O
The next reagent is NaOMe, so another alkylation:
you forgot the Br
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