[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[N:12][OH:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClN1C(=O)CCC1=O.N1C=CC=CC=1.[CH2:28]([OH:33])[CH2:29][CH2:30][CH:31]=[CH2:32].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:32][CH:31]([CH2:30][CH2:29][CH2:28][OH:33])[O:13][N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10](3,4-dimethoxyphenyl)(hydroxyimino)methane (1.05 g, 5.801 mmol) was dissolved in 30 mL of tetrahydrofuran under N2. After adding N-chlorosuccinimide (0.93 g, 6.96 mmol) and pyridine (46.9 L, 0.580 mmol) at room temperature, the reaction was continued for 30 min at 60. After cooling to room temperature, 4-pentene-1-ol (0.90 mL, 8.701 mmol) dissolved in 2 mL of tetrahydrofuran was added. Then, after adding triethylamine (0.97 mL, 6.961 mmol) dissolved in 2 mL of tetrahydrofuran, the reaction was continued for 1 hr at 50. When the reaction was completed, saturated NaHCO3 solution was added, and then the same was extracted with ethyl acetate. After drying over anhydrous MgSO4, the crude product was purified by column chromatography on silica gel (hexane/ethyl acetate=1/2, v/v) to obtain 1.38 g (90.6%) of the target compound.
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