Ethoxymethylenemalononitrile

Introduction

Ethoxymethylenemalononitrile (3) is an orange solid with a melting point of 64–66 °C. It is a functionalized malono­nitrile widely used to synthesize pyrazoles,[ ¹ ] pyrimidines[ ² ] as well as a variety of fused heterocyclic systems, like pyrazolooxazines,[ ³ ] pyrazolopyrimidines[ ⁴ ] and benzodiazepines.[ ⁵ ] It is an inexpensive reagent, but can be prepared in 94% yield by the reaction of 1,1′,1′′-[methanetriyltris(oxy)]triethane (1) and malononitrile (2) under reflux in the presence of acetic anhydride for four hours.[ ³ ]

Scheme 1 Synthesis of ethoxymethylenemalononitrile (3)

• References

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