Water → HCID 86638789, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[3-cyano-4-(4-ethynyl-phenyl)-5,5-dimethyl-5H-furan-2-ylidene]malononitrile (90 mg, 0.34 mmol) and 1-azidooctane (80 mg, 0.51 mmol) in 15 mL ethanol was stirred at 50° C. under nitrogen and a solution of sodium ascorbate (25 mg, 0.12 mmol in 1 mL water) was added, followed by copper sulfate (15 mg, 0.06 mmol in 1 mL water) solution. The resulting mixture was stirred at the same temperature for 24 h, cooled and the reaction mixture was poured into cold water (100 mL). The mixture was stirred overnight at room temperature, the precipitate formed was filtered off and air dried. The crude product was recrystallized from dichloromethane/1-propanol. Yield: 70 mg (46%) Mp (DSc): 203° C.; IR (neat) 2933, 2974, 2266, 1574, 1565 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.02 (d, J=8.4 Hz 2H), 7.87 (s, 1H), 7.85 (d, J=8.4 Hz, 2H), 4.39 (t, J=7.2 Hz, 2H), 1.94-1.96 (m, 2H), 1.82 (s, 6H), 1.20-1.31 (m, 10H), 0.82 (t, 3H); 13C NMR (CDCl3) δ 176.69, 175.14, 145.30, 136.33, 129.01, 126.40, 125.91, 121.03, 111.20, 110.47, 110.38, 100.79, 99.08, 59.85, 50.44, 31.41, 30.01, 29.41, 28.76, 28.66, 26.20, 22.31, 13.78; Anal. Calcd for C26H28N6O: C, 70.89; H, 6.41, N 19.08. Found: C, 70.59, H, 6.18; N, 19.37. UV-Vis (CH2Cl2): λmax=384 nm ε=3.01×104 L·mol−1 cm−1.

Provenance & Evidence