Tetrahydrofuran → HCID 86750904, compound

Participants

Reaction Steps

To a stirred solution of 5-[(1RS,2SR)-2-(3,4-dichlorophenyl)-1-phenylcarbamoyloxy-4-pentenyl]-1-phenyl-1,2,3-(1H)-triazole (1.0 g) in diethyl ether (4 mL), water (4 mL), and tetrahydrofuran (2 mL) was added a solution of 0.16M osmium tetroxide in water (0.22 mL). After 5 minutes sodium periodate (0.96 g) was added portionwise. After 2 hours at room temperature water was added to the reaction mixture until most of the solids dissolve. The mixture was extracted with ethyl acetate (2×50 mL); the combined organic layers dried, filtered, and the solvent evaporated to yield crude product as an oil. Chromatography, with dichloromethane:ethyl acetate (9:1) as the eluent gave the title compound 0.65 g (65%) as a white solid; NMR: 3.12 (d,2), 3.71-3.75 (m,1), 5.84 (d,1) 6.8 (dd,1), 7.03 (t,1), 7.17-7.57 (m,11), 8.01 (s,1), 9.54 (s,1); MS (CI, CH4): 495(M+1).

Provenance & Evidence