[CH3:1][O:2][C:3]1[C:4](OC)=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.C([Li])CCC.N#N.Cl[P:21]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C1C[O:37][CH2:36]C1>>[CH:22]1([P:21]([CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[C:4]2[C:5]([O:9][CH3:10])=[CH:6][C:7]([O:37][CH3:36])=[CH:8][C:3]=2[O:2][CH3:1])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1To a solution of trimethoxybenzene (1.0062 g, 6 mmol) in 20 mL of dry THF was added n-butyl lithium (2.6 mL, 2.5 M in hexane, 6.6 mmol) dropwise under N2. The mixture was stirred for 4.5 hours at room temperature, at which time the reaction system was then cooled to −78° C. Chlorodicyclohexyl phosphine was added dropwise. After the mixture is stirred for 30 minutes, the reaction system was warmed up to room temperature and stirred for another 18 hours. Extraction with ethyl acetate, washed with water, dried over anhydrous sodium sulfate, and purified by column chromatography (petroleum ether/ethyl acetate=10/1˜5/1) afforded 0.5514 g of product. The yield is 25%.
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