N,N,N',N'-Tetramethylethylenediamine → HCID 67919629, compound

Participants

Reaction Conditions

Reaction Steps

39 ml (60.5 mmol) of 1,55 molar n-butyllithium/hexane solution were added dropwise to a solution of 5.17 g (30 mmol) of N-(3-methylbenzyl)-imidazole and 3.49 g (30 mmol) of TMEDA in 60 ml of absolute THF at -70° C. The mixture was stirred for 30 minutes at -70° C., after which a solution of 4.51 g of adamantanone in 35 ml of absolute tetrahydrofuran was added dropwise at about -70° C., stirring was continued for 20 minutes at -70° C., the mixture was allowed to warm up to room temperature, 300 ml of water were added, while cooling, and the mixture was then stirred for 15 minutes at about 5° C. Thereafter, the crystalline substance which had separated out was filtered off with suction, rinsed with water and hexane, dried and boiled up with about 25 ml of CH3CN for 3 minutes. After cooling, the solid was again filtered off under suction and dried. 3.87 g (=40% yield) of pure (2-hydroxy-2-adamantyl)-1-imidazolyl-(3-tolyl)-methane of melting point 186° C. were obtained.

Provenance & Evidence