Pyridine → HCID 86674907, compound

Participants

Reaction Steps

(Aminooxy) (tert-butyl)dimethylsilane (1.00 g, 6.79 mmol) was dissolved in a mixture of dry pyridine (0.549 mL, 6.79 mmol) and dichloroethane (15 mL; dichloromethane could also be used), and a solution of 4-nitrophenyl chlorocarbonate (1.37 g, 6.79 mmol) in dichloroethane (7 mL) was added over 5 min. The resulting mixture was stirred at room temperature overnight and was then diluted with dichloromethane, washed twice with water, twice with saturated aqueous sodium bicarbonate, and brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by chromatography (90 g silica gel, 20% EtOAc/hexanes eluent) to give the title compound (1.73 g, 81%) as a white solid.

Provenance & Evidence