Methyl iodide → 2-(2-Methyl-tetrazol-5-yl)-benzaldehyde

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Reaction Steps

With the exclusion of air, 8.0 g (45.9 mmol) of 2-(tetrazol-5-yl)-benzaldehyde are added to 19 g (138 mmol) of potassium carbonate in 100 ml of DMF/dioxane (1:1) in an ice bath. 4.25 ml (68 mmol) of methyl iodide are added dropwise thereto and the reaction mixture is stirred in the ice bath for 1 hour and at RT for 1.5 hours. The mixture is stirred into 1 liter of icewater and 0.6 liter of ethyl acetate and the aqueous phase is separated off and extracted twice more with ethyl acetate. The organic phases are washed four times with water and with brine, dried (Na2SO4) and concentrated by evaporation. Column chromatography (SiO2; hexane/ethyl acetate=3:1) and stirring in hexane yield 2-(2-methyl-tetrazol-5-yl)-benzaldehyde; TLC: Rf=0.41 (hexanelethyl acetate=3:1); FAB-MS: (M+H)+=189.

Provenance & Evidence