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 Rayó; Lourdes Muñoz; Gloria Rosell; Mª Pilar Bosch; Ángel Guerrero

doi:10.1055/s-0030-1258156

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Synthesis 2010(18): 3117-3120
DOI: 10.1055/s-0030-1258156

PAPER

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 Rayó^a, Lourdes Muñoz^a, Gloria Rosell^b, Mª Pilar Bosch^a, 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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