Synthesis and X-ray crystal structure of PhC(CF3)(OH)CONEt2, PhC(CF3)(OH)CONCH2CH2OCH2CH2 and CH3C(CF3)(OH)-CON[CH2CH(CH3)(2)](2)

alpha-Hydroxy alpha-trifluoromethylated amides, PhC(CF3)(OH)CONEt2, PhC(CF3 )(OH)CONCH2CH2OCH2CH3 and CH3C(CF3)(OH)CON[CH2CH(CH3)(2)](2), were prepared under mild conditions and in excellent yields by direct nucleophilic trifl uoromethylation of the corresponding alpha-keto amides, PhCOCONEt2, PhCOCON CH2CH2OCH2CH2 and CH3COCON[CH2CH(CH3)(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 an d was refined by full-matrix least-square procedures. The presence of inter molecular hydrogen bonding has been observed in all the three cases based o n infrared spectroscopy and X-ray crystal structures. In PhC(CF3)(OH)CONEt2 and CH3C(CF3)(OH)CON[CH2CH(CH3)(2)](2) intermolecular hydrogen bonding occ urred between the hydrogen of the OH group of one molecule and oxygen of th e C=O group of a second molecule whereas in PhC(CF3)(OH)CONCH2CH2OCH2CH2 th e hydrogen of the OH group was found to be hydrogen bonded with the oxygen of the morpholine ring of a second molecule. (C) 1999 Elsevier Science S.A. All rights reserved.