December 26, 2024, 10:06:50 AM
Forum Rules: Read This Before Posting


Topic: Reformatsky reaction with ketones in presence of esters?  (Read 2838 times)

0 Members and 1 Guest are viewing this topic.

Offline fawad0418

  • Regular Member
  • ***
  • Posts: 26
  • Mole Snacks: +3/-3
Reformatsky reaction with ketones in presence of esters?
« on: February 01, 2010, 02:16:35 PM »
I want to do a reformatsky reaction with a ketone whereas same compound has one ter-butyl ester as substituent. Now the question is, if the alphabromo ester will react with esters group in substrate or with keto group???? I am trying to attach my substrate here.
thanks for guidance

Offline orgopete

  • Chemist
  • Sr. Member
  • *
  • Posts: 2636
  • Mole Snacks: +213/-71
    • Curved Arrow Press
Re: Reformatsky reaction with ketones in presence of esters?
« Reply #1 on: February 01, 2010, 02:47:11 PM »
This is just a guess, but I'd say good news and bad news. I doubt the ester is going to react. Ketones are simply more reactive. The good news is that you want to remove the t-butyl ester, good. Treat it with trifluoroacetic acid and you will have the acid. Convert it to an acid chloride and react that with a suitable reagent to introduce your nucleophile. Since the acid chloride should be more reactive, you should be able to find a solution.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Sponsored Links