Benzene → HCID 23081970, compound
Reaction equation
I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].CC(N=NC(C#N)(C)C)(C#N)C.C1C=CC=CC=1>>[C:18]1([CH2:17][CH2:16][CH:15]2[C:2]3[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]=[CH:11][C:12]=3[O:13][CH2:14]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1Participants
4
Procedure
To a solution of ethyl 3-iodo-4-{[(2E)-4-phenyl-but-2-enyl]-oxy}benzoate (13.42 g, 31.73 mmol) and AIBN (0.52 g, 3.17 mmol) in benzene (900 ml) tributyltin hydride (12 ml, 44.43 mol) was added at room temperature and the reaction mixture was warmed to reflux. After 2 h, the solvent was eliminated under vacuum. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=95/5) affording 9.14 g of the title compound (97% yield).