(Diethylamino)sulfur trifluoride → HCID 178443894, compound

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl 3-hydroxy-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 24) in dichloromethane (3 ml) was added dropwise with stirring at -70° C. to a solution of diethylaminosulphur trifluoride (0.37 g) in dichloromethane (7 ml). The mixture was stirred at -70° C. for two hours, allowed to warm to room temperature and, after a further one hour, diluted with dichloromethane, washed with water and sodium bicarbonate solution, dried over magnesium sulphate, and evaporated under reduced pressure. The residue was chromatographed on silica, using dichloromethane-ethanol (19:1) as eluant, to give diethyl 3-fluoro-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.50 g, m.p. 97°-98° C.). NMR (CDCl3): δ1.3(6H,t), 1.7-2.0(2H,m), 2.1-2.5(2H,m), 4.1(4H,m), 5.5-5.7(1H,m), 7.1-7.3(15H,m), 7.95(1H,s). M/S: M+ 507.

Provenance & Evidence