N,N,N',N'-Tetramethylethylenediamine → 1-(Methoxymethyl)-alpha,alpha-bis(p-trifluoromethylphenyl)imidazole-2-methanol

참여 물질

반응 단계

9.1 Ml. (0.015 mol) of n-butyl lithium solution (15% in n-hexane) were added dropwise with stirring at -60° C. and under a nitrogen atmosphere to a solution of 1.7 g (0.015 mol) of 1-(methoxymethyl)imidazole and 1.8 g (0.015 mol) of N,N,N',N'-tetramethylethylenediamine in 75 ml. of anhydrous tetrahydrofuran. Stirring was continued for 1.5 hours and then 2.9 g (0.0091 mol) of 4,4'-bis(trifluoromethyl)benzophenone in 50 ml. of anhydrous tetrahydrofuran were added dropwise under the same conditions, which made the colour change from light red into very dark brown. The reaction mixture was kept standing overnight at room temperature and it was then decomposed by addition of 40 ml. of water. The mixture was extracted with diethyl ether and the extract was concentrated. The residue was extracted with a mixture of 2 N hydrochloric acid and diethyl ether. The ethereal phase was dried over sodium sulphate and the ether was distilled off. The residue was boiled a few times with petroleum ether (boiling range 40°-60° C.) to remove ketone starting material and it was then once crystallised from a mixture of toluene and petroleum ether (boiling range 28°-40° C.) twice from petroleum ether (boiling range 100°-140° C.). 1-(Methoxymethyl)-α,α-bis(p-trifluoromethylphenyl)imidazole-2-methanol was obtained. Melting point 160°-161° C.

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