Organic letters

BtCH2TMS-Assisted Homologation of Carboxylic Acids: A Safe Alternative to the Arndt-Eistert Reaction

AR Katritzky, S Zhang, Y Fang

Index: Katritzky, Alan R.; Zhang, Suoming; Fang, Yunfeng Organic Letters, 2000 , vol. 2, # 24 p. 3789 - 3791

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Citation Number: 31

Abstract

One-carbon homologation of carboxylic acids is achieved by (i) treatment of an acyl chloride with 1-[(trimethylsilyl) methyl]-1 H-1, 2, 3-benzotriazole (BtCH2TMS)(1) to afford N- (acylmethyl) benzotriazoles 3a-f, followed by (ii) conversion of 3a-f with triflic anhydride into RC (OTf) CHBt 4a-f, and (iii) the subsequent reaction of 4a-c with NaOCH3 followed by 1N HCl to afford esters RCH2CO2R'7a-c in overall yields of 50-70%. For the aliphatic ...