Triphenylarsine → 3-(2-Bromo-cyclopent-1-enyl)benzoic Acid Ethyl Ester

반응식

[Br:1][C:2]1[CH2:6][CH2:5][CH2:4][C:3]=1[Sn](C)(C)C.[CH2:11]([O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](I)[CH:16]=1)[CH3:12].C1([As](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[CH2:11]([O:13][C:14](=[O:22])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([C:3]2[CH2:4][CH2:5][CH2:6][C:2]=2[Br:1])[CH:16]=1)[CH3:12]

참가 물질

실험 절차

(2-Bromo-cyclopent-1-enyl)trimethyl stannane (˜80% pure) (13.150 g, 43.7 mmol), ethyl-3-iodobenzoate (24.000 g, 87.4 mmol), triphenylarsine (4.000 g) and tris(dibenzylideneacetone)palladium (0) (1.500 g), were heated in dimethylformamide (20 mL) at 100° C., under nitrogen for 92 hours. The reaction mixture was then filtered through highflo, thoroughly washed with dichloromethane, reduced to an oil, and purified by chromatography with iso-hexane containing ether (2%–50%) to give the title compound (4.000 g, 28%).