Pyridine → HCID 178444033, compound

Participants

Reaction Steps

Hydroxylamine hydrochloride (0.29 g), then pyridine (7.7 ml), was added under nitrogen to a stirred solution of diethyl 3-oxo-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (1.0 g, prepared as described in Example 42) in ethanol (20 ml). The mixture was stirred at room temperature for three hours, then evaporated under reduced pressure. The residue was treated with water, basified to pH 8 with 1M sodium hydroxide solution, and extracted with chloroform. The organic layers were washed with brine, 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-oximino-3(1-trityl-1,2,4-triazol-3-yl)propane phosphonate (0.90 g, m.p. 190-192° C.), probably as a single geometric isomer of unknown configuration. NMR (CDCl3): δ 1.2(6H,t), 1.95-2.1(2H,m), 3.05(2H,m), 3.95(4H,m), 7.1-7.3(15H,m), 8.0(1H,s), 9.1(1H,br).

Provenance & Evidence