Synthesis and X-ray crystal structure of PhC(CF 3)(OH)CONEt 2, and CH 3C(CF 3)(OH)CON[CH 2CH(CH 3) 2] 2

Abstract

α-Hydroxy α-trifluoromethylated amides, PhC(CF 3)(OH)CONEt 2, and CH 3C(CF 3)(OH)CON[CH 2CH(CH 3) 2] 2, were prepared under mild conditions and in excellent yields by direct nucleophilic trifluoromethylation of the corresponding α-keto amides, PhCOCONEt 2, and CH 3COCON[CH 2CH(CH 3) 2] 2, respectively, with trimethyl(trifluoromethyl)silane. Their structures were confirmed by single crystal X-ray analysis. In each case, the structure was solved by direct methods and was refined by full-matrix least-square procedures. The presence of intermolecular hydrogen bonding has been observed in all the three cases based on infrared spectroscopy and X-ray crystal structures. In PhC(CF 3)(OH)CONEt 2 and CH 3C(CF 3)(OH)CON[CH 2CH(CH 3) 2] 2 intermolecular hydrogen bonding occurred between the hydrogen of the OH group of one molecule and oxygen of the CO group of a second molecule whereas in the hydrogen of the OH group was found to be hydrogen bonded with the oxygen of the morpholine ring of a second molecule.