[CH3:1][C:2](=[O:10])[CH2:3][C:4](=[O:9])[CH2:5][CH2:6][CH2:7]C.I[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I>[C:12]1([CH:3]([C:4](=[O:9])[CH2:5][CH2:6][CH3:7])[C:2](=[O:10])[CH3:1])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1
To a stirred mixture of 2,4-octanedione (568 mg, 4.0 mmol) and iodobenzene (408 mg, 2.0 mmol) in dimethylsulfoxide (10 mL) were added copper(I) iodide (380 mg, 2.0 mg) and potassium carbonate (1.10 g, 8.0 mmol). The mixture was heated at 120° C. for 4 h. The mixture was filtered through a pad of Celite and the filtrate was partitioned between ether and water. Organic layer was dried (Na2SO4) and the solvent was removed. The crude product was purified by TLC with hexane/ethyl acetate (4:1) to afford 199 mg (46%) of the title compound as colorless oil: 1H-NMR (CDCl3) δ 7.42-7.33 (3H, m), 7.18-7.15 (2H, m), 2.11 (2H, t, J=8.3 Hz), 1.87 (3H, s), 1.58-1.44 (3H, m), 1.25-1.16 (2H, m), 0.79 (3H, t, J=7.2 Hz).
Wird geladen…
