Cyclohexene → HCID 820256, compound

Participants

Reaction Steps

To a stirred solution of p-coumaric acid (3.28 g, 20 mmol) in anhydrous acetonitrile (40 mL) was added HOBt (3.24 g, 24 mmol) and EDC.HCl (4.6 g, 24 mmol) at room temperature, and the mixture was stirred at room temperature for 2 h. The resulting yellow suspension was cooled with an ice-bath, and an ice-cold solution of hydrazine (1.25 mL, 40 mmol) and cyclohexene (0.61 mL, 6 mmol) in acetonitrile (30 mL) was added in one portion. The mixture was stirred at 0° C. for 20 min and followed by an additional 1 h at room temperature. The resulting yellow suspension was filtered off, and the solid was washed with MeOH (3×30 mL), H2O (2×30 mL), saturated NaHCO3 (2×30 mL), H2O (2×20 mL) and EtOAc (2×20 mL) successively, and finally air-dried, obtaining 133 (1.3 g, 36% yield), with its identity verified by 1H NMR (300 MHz, DMSO-d6).

Provenance & Evidence