Synlett 2010(7): 1101-1103  
DOI: 10.1055/s-0029-1219796
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Patrick Le Ménez, Abdallah Hamze*, Olivier Provot, Jean-Daniel Brion, Mouâd Alami*
Univ Paris-Sud, CNRS, BioCIS UMR 8076, Laboratoire de Chimie Thérapeutique, Faculté de Pharmacie, 5 Rue J.-B. Clément, Châtenay-Malabry 92296, France
Fax: +33(1)46835828; e-Mail: mouad.alami@u-psud.fr; e-Mail: abdallah.hamze@u-psud.fr;
Further Information

Publication History

Received 17 December 2009
Publication Date:
23 March 2010 (online)

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.

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14

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