[CH:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6].Br[CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].C(=O)([O-])[O-].[Cs+].[Cs+]>CCOCC.[Cu](I)I.[CH2-]C=C.[CH2-]C=C.Cl[Pd+].Cl[Pd+].[Cl-].C12([N+]3C=CN(C45CC6CC(CC(C6)C4)C5)C=3)CC3CC(CC(C3)C1)C2>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][CH2:9][CH2:8][C:1]#[C:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH3:15]1-Hexyne (43 μl, 0.38 mmol) and ethyl 4-bromobutyrate (40 μl, 0.28 mmol) were added to a suspension of 1,3-bis(1-adamantyl)imidazolium chloride (5.2 mg, 0.014 mmol), copper iodide (4.1 mg, 0.022 mmol), allylpalladium(II) chloride dimer (2.6 mg, 0.071 mmol) and cesium carbonate (127 mg, 0.390 mmol) in anhydrous ether (0.37 ml)-anhydrous DMF (0.185 ml) at room temperature in a nitrogen stream, and the mixture was stirred at 45° C. for 17 hours. The reaction mixture was extracted with pentane. The insoluble matter was removed by filtration, and the filtrate was then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ether=50/1) to give dec-5-ynoic acid ethyl ester (40 mg, 73%).
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