January 19, 2022, 05:14:31 PM
Forum Rules: Read This Before Posting


Topic: Stuck on Claisen(?) reaction  (Read 1998 times)

0 Members and 1 Guest are viewing this topic.

Offline jezzielee

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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?
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline jezzielee

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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.
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline jezzielee

  • New Member
  • **
  • Posts: 3
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +405/-70
  • Gender: Male
    • My research history
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
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Sponsored Links