Triethylamine → 1-(p-cyanophenylmethyl)-5-(2-formylethyl)-1H-imidazole

Participants

Reaction Steps

A solution of 0.14 ml of dimethylsulfoxide in 5 ml of methylene chloride is cooled to -78° under N2 and 0.1 ml of oxalyl chloride is added dropwise. After 30 min, a solution of 0.24 g of 1-(p-cyanophenylmethyl)-5-(3-hydroxypropyl)-1H-imidazole in 1 ml of methylene chloride and 0.2 ml of dimethylsulfoxide is added slowly. The reaction mixture is stirred at -78° for 2 h and 1 ml of triethylamine is added slowly. The reaction mixture is allowed to warm slowly to room temperature, diluted with 30 ml of methylene chloride and washed three times with 10 ml of water. The organic phase is dried over sodium sulfate and evaporated to yield the title compound a) as an oil, NMR (60 MHZ): δ5.15 (s, 2H), 9.65 (s, 1H).

Provenance & Evidence