Title:One Pot Conversion of Carboxylic Acid to Ketone Using Trimethylsilyl Chloride
Volume: 8
Issue: 2
Author(s): Habtamu G. Mekonnen and Samaresh Jana*
Affiliation:
- Department of Chemistry, School of Applied Sciences, KIIT-Deemed to be University, Bhubaneswar-751024, Odisha,India
Keywords:
One-pot conversion, carboxylic acid, ketone, trimethylsilyl chloride, aromatic, organolithium reagent.
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.
