Topic: Stuck on Claisen(?) reaction (Read 2793 times)

jezzielee · « **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!

discodermolide · « **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?

jezzielee · « **Reply #2 on:** June 19, 2014, 03:45:37 PM »

Quote from: discodermolide 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?

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

discodermolide · « **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.

jezzielee · « **Reply #4 on:** June 19, 2014, 04:04:36 PM »

Quote from: discodermolide on June 19, 2014, 03:51:49 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

discodermolide · « **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

Topic: Stuck on Claisen(?) reaction (Read 2793 times)

jezzielee

Stuck on Claisen(?) reaction

discodermolide

Re: Stuck on Claisen(?) reaction

jezzielee

Re: Stuck on Claisen(?) reaction

discodermolide

Re: Stuck on Claisen(?) reaction

jezzielee

Re: Stuck on Claisen(?) reaction

discodermolide

Re: Stuck on Claisen(?) reaction

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