[CH2:1]([O:8][CH2:9][CH:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1C=CC=CC=1)C=C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:24]I>ClCCl.S([O-])([O-])(=O)=S.[Na+].[Na+]>[CH2:1]([O:8][CH2:9][CH:10]1[CH:16]([CH2:17][I:24])[O:15][C:14](=[O:23])[NH:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1A mixture of benzyl [1-(benzyloxy)but-3-en-2-yl]carbamate (3.0 g, 9.6 mmol) and iodine (4.9 g, 19 mmol) in dichloromethane (200 mL) was stirred at 20° C. for 16 hours. The reaction mixture was diluted with aqueous sodium thiosulfate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to give the crude product residue. The crude product residue was purified by silica gel chromatography (ethyl acetate/petroleum ether) to give 4-[(benzyloxy)methyl]-5-(iodomethyl)-1,3-oxazolidin-2-one. MS ESI calc'd. for C12H15INO3 [M+H]+ 348. found 348. 1H NMR (300 MHz, CDCl3) δ 7.40-7.27 (m, 5H), 5.53 (s, 1H), 4.57 (s, 2H), 4.37-4.34 (m, 1H), 3.82-3.80 (m, 1H), 3.67-3.51 (m, 2H), 3.38-3.32 (m, 2H).
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