Sodium Hydroxide → 4-Ethenylquinoline

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[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH:11]=O)=[CH:3][CH:2]=1.[I-].[C:14]1(C([PH3+])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>C1C=CC=CC=1>[CH:11]([C:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:1]=[CH:2][CH:3]=1)=[CH2:14]

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온도: 45 °C

실험 절차

A solution of 4-quinolinecarboxaldehyde (5 g; 3.18×10-2 mol) in 32 ml of benzene, containing triphenylmethylphosphonium iodide (26 g; 6.36×10-2 mol), is added under an inert atmosphere to sodium hydroxide solution (96 ml; 5N). The two-phase system is stirred at 45° C. for 30 minutes. After allowing the phases to separate by settling, the aqueous phase is extracted with ethyl acetate (3×100 ml). The organic phases are combined and washed with 1N HCl solution (2×30 ml), then the aqueous phase is neutralized with NaHCO3 and extracted with methylene chloride (3×100 ml). The organic phase is dried over MgSO4. The desired product is purified by chromatography on a MERCK F254 silica column (eluent=cyclohexane/AcOEt, 8:2). Yield=2.8 g (60%).