CuI mediated efficient synthesis of β-Hydroxy esters by the reformatsky reaction
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School of Pharmacy,Gannan Medical University,Ganzhou

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O625.3

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    Abstract:

    A simple and efficientcuprous iodide-mediated catalytic system of reformatsky reaction has been described. The reformatsky reaction of ethyl iodoacetate2a with aromatic aldehydes 1/ketones3 was efficiently catalyzed by zinc powder and mediated by the cheap and easily available cuprous iodide. With acetonitrile/water mixed solvent as the reaction solvent, 32 β-hydroxyl esters I~XXXII were synthesizedwith high yield (82%~95% yield) under mild conditions. The structures of products obtained were confirmed by 1 HNMR, 13 CNMR and MS. According to the previous research and the related literature, the possible reaction mechanism was proposed. In addition, the catalytic methodology can be scaled up to the gram scale.With benzaldehyde 1a (10 mmol) and ethyl iodoacetate 2a (15 mmol) as raw materials, β-hydroxyl ester I (1.94 g, yield 92%) was obtained from with high yield.

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History
  • Received:July 07,2022
  • Revised:August 30,2022
  • Adopted:September 07,2022
  • Online: June 12,2023
  • Published:
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