Potassium Carbonate → Methyl 2-(1H-tetrazol-1-yl)propanoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 2-bromopropionate (66.8 g), 1H-tetrazole (28.02 g), anhydrous potassium carbonate (110 g) and acetone (1000 cm3) was stirred together at the ambient temperature (ca. 18° C.) for 1 hour and then at reflux temperature for four hours. After keeping the mixture for a further 16 hours at the ambient temperature the insoluble component was removed by filtration and the filtrate concentrated by evaporation of the solvent under reduced pressure. The residual oil (60 g) was subjected to distillation and the fraction having a boiling point range from 78°-93° C. at 0.35 to 2.5 mm Hg collected to yeild methyl 2-(1,2,3,4-2H-tetrazol-2-yl)propionate (A; 22.3 g). The undistillable residue was dissolved in dichloromethane and purified by elution through a short silica column. The collected eluate was concentrated by evaporation of the solvent under reduced pressure to yield methyl 2-(1,2,3,4-1H-tetrazol-1-yl)propionate (B; 35 g, 99% pure by gas/liquid chromatographic analysis).

Provenance & Evidence