[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17]C(C)(O)C)=[CH:12][CH:11]=1.[H-].[Na+].C(OC(C)C)(C)C.Cl>C1(C)C=CC=CC=1.O>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:11][CH:12]=1)#[CH:17]Under a nitrogen atmosphere, to a solution of 4-[4-(6-methoxyhexyloxy)phenyl]-2-methyl-3-butyn-2-ol (3.0 g) in toluene (18 ml) was added sodium hydride (abt. 60% in oil suspension), and the mixture was refluxed for 2 hours. After cooling, to the reaction mixture was added isopropyl ether (100 ml) and water (100 ml), and neutralized by 1N-hydrochloric acid. The organic layer was separated, washed with water and brine, dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude red oil. The crude red oil was purified by silica gel chromatography (10:1 hexane-ethyl acetate) to give 1-ethynyl-4-(6-methoxyhexyloxy)benzene (2.39 g) as an orange powder.
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