Water → 3-Ethyl-5-methyl-2-naphthalen-1-yl-3h-imidazole-4-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester (1.5 g) in DMF (30 ml) is added NaH (320 mg, 60%) at rt. The solution is stirred for 30 min, and EtI (0.6 ml) is added. After 30 min, the mixture is cooled to 0° C. and H2O is added. The mixture is then extracted with EtOAc. The extracts are combined, dried, evaporated and purified by column (EtOAc:Hexanes 1:1) to give 3-ethyl-5-methyl-2-naphthalen-1-yl-3H-imidazole-4-carboxylic acid ethyl ester [LCMS 309.4 (M+1); δ 4.10 ppm (CH2CH3)] and its regioisomer 1-ethyl-5-methyl-2-naphthalen-1-yl-1H-imidazole-4-carboxylic acid ethyl ester [LCMS 309.4 (M+1); δ 3.72 ppm (CH2CH3)].

Provenance & Evidence