[C:1]([OH:7])(=[O:6])[CH2:2][CH2:3][C:4]#[CH:5].I[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(NCC)C.[Cu]I>[C:9]1([C:5]#[C:4][CH2:3][CH2:2][C:1]([OH:7])=[O:6])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1A solution of pent-4-ynoic acid (1.0 g, 10 mmol), iodobenzene (2.3 ml, 20 mmol), copper(I) iodide (75 mg, 0.40 mmol) and dichlorobis(triphenylphosphine)-platinum(II) (140 mg, 0.20 mmol) in 20 mL of diethylamine was stirred at rt for 3 days. The volatile material are evaporated by a rotary evaporator and the resulting residue was dissolved in 50 mL dichloromethane and washed with 1 M HCl (50 mL). The dichloromethane layer was dried over sodium sulfate and evaporated to dryness under vacuum. The residue was purified by column chromatography (ethyl acetate/dichloromethane) to afford 5-phenylpent-4-ynoic acid (0.49 g).
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