Tributyltin Hydride in NMP-Promoted Reduction of Acid Chlorides to Aldehydes under Transition-Metal-Free Conditions

Abstract

Tributyltin hydride in N-methyl-2-pyrrolidinone (NMP) was used for the partial reduction of various functionalized acid chlorides at room temperature. This transition-metal-free procedure allows the synthesis of a range of (hetero)aromatic- and aliphatic aldehydes in good to excellent yields.

acid chlorides - aldehydes - reduction - tributyltin hydride - N-methyl-2-pyrrolidinone - free-metal conditions

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Typical procedure: Acid chloride 1 (1 mmol) was dissolved in NMP (1 mL) under an argon atmosphere. Bu₃SnH (1.05 mmol) was added dropwise and the resulting mixture was stirred at r.t. for 1 h. Then, H₂O (2 mL) was added and the mixture was extracted with EtOAc (3 × 5 mL). The combined organic phases were washed with an aq sat. NH₄Cl (3 × 5 mL), dried over MgSO₄ and concentrated. The crude mixture was purified by column chromatography on silica gel to give the desired aldehyde 2

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