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Synthesis 2010(18): 3117-3120  
DOI: 10.1055/s-0030-1258156
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Improved Microwave-Assisted Ring Opening of 1,1,1-Trifluoro-2,3-epoxypropane: Synthesis of New 3-Alkoxy-1,1,1-trifluoropropan-2-ols

Josep Rayóa, Lourdes Muñoza, Gloria Rosellb, Mª Pilar Boscha, Ángel Guerrero*a
a Department of Biological Chemistry and Molecular Modelling, IQAC (CSIC), Jordi Girona 18-26, 08034 Barcelona, Spain
b Department of Pharmacology and Therapeutic Chemistry, Unity Associated to CSIC, Faculty of Pharmacy, University of Barcelona, Avda. Diagonal s/n., 08028 Barcelona, Spain
Fax: +34(932)045904; e-Mail: angel.guerrero@iqac.csic.es;
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Publication History

Received 14 May 2010
Publication Date:
07 July 2010 (online)

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Abstract

A highly efficient and environmentally friendly method for the synthesis of 3-alkoxy-1,1,1-trifluoropropan-2-ols is presented. The approach involves ring-opening reaction of 1,1,1-trifluoro-2,3-epoxypropane with structurally different long-chain alcohols under microwave irradiation at room temperature in the absence of solvent. These chemicals are precursors of the corresponding tri­fluoromethyl ketones, potent inhibitors of human and murine liver microsomes and porcine liver esterase.

Key words

1,1,1-trifluoro-2,3-epoxypropane - ring opening - tri­fluoro­methyl carbinols - trifluoromethyl ketones - microwave catalysis

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