Trityl chloride → 2-Trityl-5-methyl tetrazole

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-methyl-1H-tetrazole (1.513 g, 18.00 mmol), tetrabutylammonium bromide (0.029 g, 0.090 mmol) and sodium hydroxide (18.90 mL, 18.90 mmol) in dichloromethane (DCM) (25 mL) stirred under nitrogen at room temperature, was added (chloromethanetriyl)tribenzene (5.02 g, 18 mmol). The reaction mixture was stirred at 20° C. for 72 hours. The reaction was quenched with water, then partitioned between dichloromethane (10 mL) and water (25 mL). The organic phase was separated (hydrophobic frit) and the aqueous phase re-extracted (stirred for 5 min) with additional DCM (10 mL), then separated with a hydrophobic frit. The combined organic fractions were washed with water (2×25 mL), 5% aqueous sodium bicarbonate (10 mL) and brine (10 mL). The organic phase was evaporated in vacuo to give a white solid. Recrystallisation from hot ethyl acetate (8 mL/g) provided the product as a white solid (2.2 g). LCMS RT 1.35 mins.

Provenance & Evidence