I[C:2]1[C:3](=[O:7])[CH2:4][CH2:5][CH:6]=1.[Cl:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.O1CCCC1.O>[Cl-].[NH4+].[Ag-]=O.C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[C:3](=[O:7])[CH2:4][CH2:5][CH:6]=2)=[CH:11][CH:10]=14.8 g 2-Iodo-cyclopent-2-enone (prepared as described in Org. Lett. 6, 2004, page 3289), 5.4 g 4-chlorophenylboronic acid, 8.5 g silver(I)oxide, 0.425 g triphenylarsine and 0.265 g Pd(C6H5CN)2Cl2 were added to 90 ml tetrahydrofurane and 20 ml water. The reaction mixture was stirred under nitrogen atmosphere for 16 hours. The reaction mixture was diluted with ammonium chloride, filtered and extracted twice with ethyl acetate. The residue was purified by chromatography and the solvent was evaporated. 3.44 g 2-(4′chlorophenyl)cyclopent-2-enone were obtained (m.p. 71-72° C.).
Loading…
