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Facile Synthesis of β-Ketoesters by Indium-Mediated Reaction of Acyl Cyanides with Ethyl Bromoacetate under Ultrasonication

  • Park, Young-Sang (Department of Advanced Materials Chemistry, Korea University) ;
  • Han, Jung-Hwa (Department of Advanced Materials Chemistry, Korea University) ;
  • Yoo, Byoung-Seung (Department of Food Science and Technology, Dongguk University) ;
  • Choi, Kyung-Il (Biochemicals Research Center, Korea Institute of Science and Technology) ;
  • Kim, Joong-Hyup (Biochemicals Research Center, Korea Institute of Science and Technology) ;
  • Yoon, Cheol-Min (Department of Advanced Materials Chemistry, Korea University) ;
  • Yoo, Byung-Woo (Department of Advanced Materials Chemistry, Korea University)
  • Published : 2005.06.20
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Abstract

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References

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  21. A typical procedure: Indium metal (173 mg, 1.5 mmol) was added to a solution of ethyl bromoacetate (334 mg, 2.0 mmol) in THF (3 mL) and the resulting mixture was stirred for 30 min at room temperature. A solution of benzoyl cyanide (131 mg, 1.0mmol) in THF (1 mL) was then slowly added and the mixture was stirred for 2 h at room temperature under sonication. After complete conversion, as indicated by TLC, the reaction mixture was poured into water and extracted with ether. The combined organic layer was washed with brine, dried over anhydrous $Na_2SO_4$, and concentrated in vacuo to yield crude product, which was purified by column chromatography on silica gel(hexane : ethyl acetate = 6 : 1) to afford ethyl phenylacetoacetate(169 mg, 88%).

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