N,N,N',N'-Tetramethylethylenediamine → 3-Methoxyphenyl-(2-hydroxy-2-adamantyl)-1-imidazolylmethane

Participants

Reaction Conditions

Reaction Steps

55 ml (85 mmol) of a 1.55 molar solution of n-butyllithium in hexane were added dropwise to a solution of 7.52 g (40 mmol) of N-(3-methoxybenzyl)-imidazole and 4.65 g (40 mmol) of TMEDA in 90 ml of absolute THF at -70° C. The mixture was stirred for a further 20 minutes at -70° C., and a solution of 6.01 g (40 mmol) of adamantanone in 30 ml of absolute THF was then added dropwise at -70° C. in the course of about 10 minutes. The procedure was then continued as described in Example 100. The residue (13 g) from the CH2Cl2 extract was crystallized from acetonitrile. 7.5 g of pure 3-methoxyphenyl-(2-hydroxy-2-adamantyl)-1-imidazolylmethane of melting point 182° C. were obtained.

Provenance & Evidence