Malononitrile → HCID 59541855, compound

Participants

Reaction Steps

The title compound was prepared by the method of Dunham et al. (Synthesis 2006 (4), 680). 1,4-Cyclohexanedione monoethylene ketal (3.15 g, 20.0 mmol) was dissolved in anhydrous 2-propanol (20 mL), treated with warm malononitrile (Aldrich, 0.70 mL, 11.1 mmol) via syringe, and the reaction was cooled in ice and treated with powdered sodium borohydride (Aldrich, 0.42 g, 11.1 mmol). After stirring for 2 h in ice, the reaction was quenched with water and acidified to pH 6 with 1N aqueous HCl, and the resulting suspension was extracted thrice with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give a pale yellow oil, which was purified by flash column chromatography on silica gel (gradient elution, 30 to 80% EtOAc in hexanes) giving the title compound as a pale yellow crystalline solid.

Provenance & Evidence