Ethyl Acetate → 4-(1H-1,2,3,4-tetrazol-5-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

Trimethylsilyl azide (25 g) and dibutyltin oxide (8.8 g) were added to a solution of 4-cyanobenzaldehyde (13 g) in toluene (200 ml). The reaction was stirred with warming to 50° C. over 1 hr, and then warmed to 96° C. over 30 minutes and maintained at that temperature for 3 hours. The solvent was evaporated in vacuo to afford an orange oil which was purified by column chromatography over silica gel (ethyl acetate). The crude product was dissolved in refluxing toluene and allowed to cool with stirring overnight. The resulting slurry was granulated in an ice-bath for 1 hour, filtered and washed with cold toluene. The filtrate was evaporated in vacuo to afford a solid. The solid was dissolved in refluxing ethyl acetate (250 ml) and concentrated to 60 ml by rotary evaporation. The solution was cooled to room temperature and then granulated in an ice bath. The thick slurry was collected by filtration, washed and dried, with warming, in a vacuum oven to afford the title compound, 12 g.

Provenance & Evidence