Hydrochloric Acid → 1-[2-(3-methylphenyl)-2H-tetrazol-5-yl]ethanone

Participants

Reaction Conditions

Reaction Steps

Methylmagnesium bromide (1070 mL, 1.50 mol, 1.4 M in tetrahydrofuran/toluene) in triethylamine (520 mL, 3.74 mol) was added via an addition funnel to a stirred solution of ethyl 2-(3-methylphenyl)-2H-tetrazole-5-carboxylate in dry toluene (1000 mL) at −10° C. for 5 hours. The mixture was continued to stir at −10° C. overnight. A cooled (+3° C.) solution of hydrochloric acid (37%, 500 mL) and water (500 mL) was added over 2 hours 20 minutes. The layers were separated and the organic layer was washed with water (500 mL) and brine (2×250 mL). The aqueous layer was extracted with toluene (3×500 mL) and the toluene was washed with brine (2×250 mL). The combined organic extracts were concentrated and purified on silica using dichloromethane as eluent. The concentrated product residue was triturated with petroleum ether, filtrated and dried under reduced pressure at room temperature to give the title product (90.86 g, 60%).

Provenance & Evidence