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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
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Overview
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Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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A highly efficient macrolactonization method via ethoxyvinyl ester.

Yusuke Ohba1, Mayuko Takatsuji, Kenji Nakahara

  • 1Graduate School of Pharmaceutical Sciences, Osaka University 1-6, Yamada-oka, Suita, Osaka, Japan.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 21, 2009
PubMed
Summary

This study introduces a novel macrolactonization method using ethoxyvinyl esters (EVEs) for efficient synthesis of various lactone sizes. The procedure offers good yields, especially for 9- to 14-membered macrolactones, and is suitable for sensitive substrates.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Macrolactonization is a key reaction in synthesizing complex organic molecules.
  • Existing methods often face limitations with sensitive functional groups or specific ring sizes.

Purpose of the Study:

  • To develop a highly efficient and versatile macrolactonization procedure.
  • To enable the synthesis of diverse lactone structures, including medium to large rings.
  • To provide a method compatible with acid- and base-sensitive substrates.

Main Methods:

  • Preparation of ethoxyvinyl esters (EVEs) from hydroxycarboxylic acids using a Ruthenium (Ru) catalyst.
  • Macrolactonization of EVEs catalyzed by p-toluenesulfonic acid (pTsOH) in 1,2-dichloroethane (DCE) at 80°C.
  • Demonstration of the method's applicability to substrates with nucleophilic amine functions.

Main Results:

  • The ethoxyvinyl ester (EVE) method successfully produced various-sized lactones.
  • Good yields were achieved for 9- to 14-membered macrolactones.
  • The Ru catalyst retained activity even in the presence of nucleophilic amine groups.
  • The method proved effective for a complex substrate (compound 14) with multiple functional groups.

Conclusions:

  • The ethoxyvinyl ester (EVE) mediated macrolactonization is a highly efficient synthetic strategy.
  • This method is particularly valuable for synthesizing medium to large ring lactones.
  • The procedure's compatibility with sensitive functional groups and its robustness make it a significant advancement in organic synthesis.