N,N,N',N'-Tetramethylethylenediamine → HCID 178440152, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 4-(1-methylethyl)-5-phenyl-1-(α-ethoxyethyl)imidazole (13.9 g, 0.054 mole) in 210 ml of dry tetrahydrofuran was added 9.45 ml of tetramethylethylenediamine (0.06 moles). The reaction was cooled to -78° C. and 56.15 ml of 1.66M n-butyl lithium in hexane was added dropwise. After stirring the mixture for 20 minutes, hexafluoroacetone (14.0 ml) was condensed and added dropwise. The reaction was stirred an additional hour at -78° C. and then 275 ml of saturated aqueous sodium bicarbonate solution was added dropwise. After warming to room temperature, the layers were separated and the aqueous was extracted with ethyl acetate. The organic layers were combined and concentrated in vacuo. The residue was stirred overnight in 350 ml of ethanol and 350 ml of 2N aqueous hydrochloric acid. The ethanol was evaporated and the reaction mixture was basified to a pH of 8 with saturated aqueous potassium carbonate. The mixture was extracted with ether, washed with 10% aqueous sodium bicarbonate and dried over anhydrous magnesium sulfate. The residue was purified via flash chromatography on silica gel (98:2 hexane/ethyl acetate) to afford 13.19 g (70%) of the product which was recrystallized from hexane to give a white crystalline solid, m.p. 80°-81° C.

Provenance & Evidence