Staudinger Reaction

To a solution of the organic azide (2.31 mmol, 1.0 eq) in THF (20 mL) was added triphenylphosphine (2.0 eq) and water (10.0 eq) at room temperature. The reaction mixture was heated at 65 °C. After stirring for 6 h, the mixture was allowed to cool to room temperature and di-tert-butyl dicarbonate (2.0 eq) was added at the same temperature. After stirring for 1 h, the mixture was poured into water and then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the desired product (90% yield).