Diazald → Diazomethane

Participants

Reaction Conditions

Reaction Steps

Diazomethane was prepared from Diazald (21.5 g), KOH (6.6 g) in 2-(2-ethoxyethoxy)ethanol (35 mL). To the diazomethane solution in Et2O was added ethyl 2,3-dimethylcycloprop-2-enecarboxylate as obtained above. The mixture was stirred at 0° C. for 14 days in the dark. A solution of acetic acid in Et2O was added to quench off remaining diazomethane and the volatiles were removed in vacuo. Remaining starting material was removed by Kugelrohr distillation to afford ethyl 1,5-dimethyl-2,3-diaza-bicyclo[3.1.0]hex-2-ene-6-carboxylate (1.25 g, 6.9 mmol) as a yellowish oil in 10% yield over 2 steps.

Provenance & Evidence