Maleic Anhydride → HCID 58807382, compound

Participants

Reaction Steps

Under nitrogen, a solution of 3-methyl-2-[1-phenyl-meth-(E)-ylidene]-2,3,3a,4,7,7a-hexahydro-4,7-methano-inden-1-one (5) (250 mg, 1 mmol., 1 eq.) and maleic anhydride (490 mg, 5 mol., 5 eq.) in dichloromethane (10 cm3) was treated with a 1.0 M solution of MeAlCl2 in hexane (1.1 cm3, 1.1 mmol., 1.1 eq.). This mixture was heated to reflux for 5 hours. Silica (ca. 2.5 g) was added and the solvent was removed under reduced pressure. Flash column chromatography (Hex-EtOAc; 3:1) gave 4-methyl-5-[1-phenyl-meth-(E)-ylidene]-cyclopent-2-enone (6) (compound CTC-150) (138 mg, 75%) as a colourless solid. Rf=0.5 (Hex-EtOAc; 3:1); δH (400 MHz, CDCl3) 1.22 (3H, d, J 7.0 Hz, CH3), 3.84-4.00 (1H, m, CH), 6.40 (1H, dd, J 1.75, 5.75 Hz, CH), 7.39-7.44 (4H, ArH), 7.54 (2H, d, J 7.0 Hz, AH, 7.60 (1H, ddd, J 1.0, 2.5, 5.75 Hz, CH); δC (100 MHz, CDCl3) 16.3, 38.8, 128.7, 129.3, 130.6, 131.7, 133.6, 134.8, 138.3, 163.9, 197.4; Found C, 84.66; H, 6.60%, C13H12O requires C, 84.78; H, 6.57%.

Provenance & Evidence