Synthesis and characterization of novel trifluoromethyl-containing alcohols with Ruppert's reagent

Abstract

Synthesis and characterization of novel new trifluoromethyl-containing alcohols using Ruppert's reagent [(trimethyl)trifluoromethylsilane] (1) are reported. The reactions of 1 with various ketones and aldehydes, such as tetraphenylcyclopentadienone (2a), 9,10-anthraquinone (2b), pyrenaldehyde (2c), 2,6-dimethyl-para-anisaldehyde (2d), and 2,3(methylenedioxy)benzaldehyde (2e) in the presence of a catalytic amount of tetrabutylammonium fluoride in THF led to the formation of the corresponding trifluoromethylated silyl ether derivatives 3a-e in almost quantitative yields. Acid hydrolysis of 3a-e gave the desired trifluoromethylated alcohol derivatives (4a-e) in excellent isolated yields. Compounds were characterized by IR, NMR (1H, 19F, 13C NMR), GCMS, and elemental analysis. Single crystal X-ray structures of 4a and 4b support the proposed products. © 2011 Elsevier B.V. All rights reserved.