One-Pot Conversion of Carboxylic Acid to Ketone Using Trimethylsilyl Chloride

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Author(s): Habtamu Gelaw Mekonnen, Samaresh Jana*

Journal Name: Current Organocatalysis

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Abstract:

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

Objective: We aimed to develop a simple one pot reaction for the conversion of carboxylic acid to 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 has been converted to the corresponding trimethylsilyl ester using trimethylsilyl chloride in the presence of a base. A suitable organometallic reagent can interact 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 have been converted to 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 carboxylic acid to ketone has been reported in a one pot fashion, where carboxylic acid has been transformed to its silyl ester. Organolithium reagents were used as nucleophile for our reaction purpose, whereas the organomagnesium reagents were not useful for this transformation. Aliphatic, aromatic and heteroaromatic carboxylic acids have been converted to the ketones following a simple process.

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

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Article Details

(E-pub Ahead of Print)
DOI: 10.2174/2213337207999200727143040
Price: $95

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