2-Cyclohexylidenemalononitrile → HCID 86665182, compound

Participants

Reaction Steps

A solution of vinylmagnesium bromide (1 M in THF, 24 mL, 24 mmol) was added dropwise over 2 min to a solution of the product from Example 145A (730 mg, 4.99 mmol) in THF (8 mL) under nitrogen. The reaction mixture was stirred at room temperature for 13 hours, then quenched by cautious addition of saturated aqueous NH4Cl (25 mL). The mixture was stirred vigorously for 10 minutes, and then diluted with water (10 mL). The aqeuous layer was separated and extracted with EtOAc (25 mL). The combined organic phase was concentrated under vacuum, and the residue was purified by flash chromatography (silica gel eluted with hexanes-EtOAc, 90:10-80:20) to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 1.24-1.37 (m, 2H), 1.40-1.68 (m, 6H), 1.85-2.03 (m, 2H), 3.56 (s, 1H), 5.39 (d, J=17.4 Hz, 1H), 5.53 (d, J=10.7 Hz, 1H), 5.73 (dd, J=17.5, 10.7 Hz, 1H).

Provenance & Evidence