Acetaldehyde → ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonate

Participants

Reaction Steps

A round-bottom flask was charged with Preparation 22, 5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazole (191 g, 692 mmol), 4-dimethylaminopyridine (4.27 g, 34.6 mmol), THF (1.72 L), acetaldehyde (43 mL, 760 mmol), and triethylamine (107 mL, 762 mmol). The reaction solution was stirred and then ethyl chloroformate (86.2 mL, 97% by mass, 692 mmol) was added. The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted with EtOAc (965 mL) and H2O (965 mL). The layers were separated. The aqueous layer was extracted with EtOAc (965 mL). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to afford ethyl 1-[5-(4-iodo-1-methyl-1H-pyrazol-5-yl)-2H-tetrazol-2-yl]ethyl carbonate as a colorless oil (261 g, 96% yield).

Provenance & Evidence