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Synlett 2010(17): 2644-2648  
DOI: 10.1055/s-0030-1258580
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

One-Step Oxidation of 2-Arylpropanols to 2-Arylpropionic Acids: Improving Sustainability in the Synthesis of Profens

Paola Galletti, Matteo Pori, Daria Giacomini*
Department of Chemistry, ‘G. Ciamician’ University of Bologna, Via Selmi 2, 40126 Bologna, Italy
Fax: +39(051)2099456; e-Mail: daria.giacomini@unibo.it;
Further Information

Publication History

Received 28 July 2010
Publication Date:
23 September 2010 (online)

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Abstract

Three oxidation procedures were evaluated for the synthesis of optically pure 2-arylpropionic acids. Efficient, mild, and eco-friendly conditions were obtained with the system comprising TEMPO, NaClO, and NaClO2. Thus a series of profens were obtained in good to excellent yields.

Key words

oxidation - alcohols - carboxylic acids - anti-inflammatory agents - profens - TEMPO

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Compounds 1b-g were obtained by BH3˙SMe2 reduction from commercially available racemic acids. Compound 1h was easily obtained in a three steps synthesis starting from ketoprofen (EtOH, BF3˙OEt2 cat.; ethylene glycol, TsOH cat. in toluene; LiAlH4 in THF).

15

Referred to reported data, see ref. 7.