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Current Organocatalysis

Author(s): Habtamu G. Mekonnen and Samaresh Jana*

DOI: 10.2174/2213337207999200727143040

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One Pot Conversion of Carboxylic Acid to Ketone Using Trimethylsilyl Chloride

Page: [195 - 199] Pages: 5

  • * (Excluding Mailing and Handling)

Abstract

Background: Ketone is abundant in many natural products and pharmaceuticals. It is believed to be one of the important functional groups in organic chemistry. To date, several research approaches have been made to access ketone from readily available starting materials. One such notable transformation consists of the conversion of a carboxylic acid into the corresponding ketone in a one-pot manner.

Objective: We aimed to develop a simple one-pot reaction for the conversion of a carboxylic acid into ketone. This reaction could be useful to convert all types of carboxylic acid to ketone in a facile manner.

Methods: In this procedure, a carboxylic acid was converted into the corresponding trimethylsilyl ester using trimethylsilyl chloride in the presence of a base. A suitable organometallic reagent interacted with the ester formed at -20°C to produce the corresponding ketone.

Results: Under the optimized reaction conditions, various aromatic, aliphatic and heteroaromatic carboxylic acids were converted into the corresponding ketones using organolithium reagents, in a one-pot manner. Moderate to good yields of the desired ketones were observed in most of the transformations.

Conclusion: Conversion of a carboxylic acid into ketone has been reported in a one-pot fashion, where carboxylic acid has been transformed into its silyl ester. Organolithium reagents were used as nucleophiles for reaction purposes. It was observed that the organomagnesium reagents were not useful for this transformation. Aliphatic, aromatic and heteroaromatic carboxylic acids have been converted into the ketones following a simple process.

Keywords: One-pot conversion, carboxylic acid, ketone, trimethylsilyl chloride, aromatic, organolithium reagent.

Graphical Abstract

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