[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][C:12](=[O:14])[NH:11][CH:10]2[CH2:15]O)=[CH:5][CH:4]=1.ClC(F)C(N(CC)CC)(F)[F:20]>C(Cl)Cl.C(OCC)(=O)C>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[O:13][C:12](=[O:14])[NH:11][CH:10]2[CH2:15][F:20])=[CH:5][CH:4]=1To a solution of 250 mg (1.0 mmole) of 5-(4-methylthiophenyl)-4-hydroxymethyl-oxazolidin-2-one in 30 ml of methylene chloride was added 0.21 ml (1.3 moles) of N-(2-chloro-1,1,2-trifluoroethyl)-diethylamine. The reaction mixture was heated in a teflon bomb at 110° C for 1.5 hours. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed twice with water, dried and concentrated. Chromatography on silica gel afforded 150 mg (0.62 mmole), 62% of 5-(4-methylthiophenyl)-4-fluoromethyl-oxazolidin-2-one.
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