[C:1]1(=[C:7]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[C:8]#[N:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]2([C:8]#[N:9])[C:1]3([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[O:26]2)=[CH:11][CH:12]=12.0 g of the product from Stage 1 was refluxed for 8 hours with 2.0 g of m-chloro-perbenzoic acid, in dichloromethane. The reaction mixture was cooled to room temperature and filtered to remove precipitated m-chloro-perbenzoic acid. The filtrate was washed with saturated sodium bicarbonate solution, and the dichloromethane layer was then dried over sodium sulphate. The solvent was distilled under reduced pressure, and the residue purified by column chloromatography using a hexane:benzene (8:2) mixture as the mobile phase.
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