反应详情

p-Toluenesulphonyl chloride (2.74 g, 14.36 mmol) and Et3N (1.45 g, 14.36 mmol) were added to 5-hydroxymethyl-1,3-oxazolidine-2-one (1.40 g, 11.97 mmol) dispersed in 20 mL of dichloromethane and stirred overnight at room temperature under N2. After completion of the reaction (TLC), the solvent in the reaction mixture was evaporated and the residue was purified by column chromatography employing EtOAc-hexane (70:30) as eluent to afford 5-tosyloxymethyl-1,3-oxazolidine-2-one in 80% yield. m.p. 96-99° C.; [α]27D=+45.40 CHCl3); IR (KBr) 3302, 2980, 2925, 2871, 1757, 1694, 1357, 1184, 1090, 996, 965 cm1; 1HNMR (200 MHz, CDCl3) δ 2.47 (s, 3H), 3.40-3.50 (m, 1H), 3.64-3.74 (m, 1H), 4.14 (d, 2H, J=4.4 Hz), 4.71-4.82 (m, 1H), 7.35 (d, 2H, J=8.2 Hz), 7.78 (d, 2H, J=8.2 Hz); Mass (EI) 271, 207, 173, 155, 139, 91.

1. customAfter completion of the reaction (TLC)
2. customthe solvent in the reaction mixture was evaporated
3. customthe residue was purified by column chromatography