p-Toluenesulfonyl azide → (1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of sodium hydride (0.32 g, 13.2 mmol) in 100 mL 6/1 benzene/tetrahydrofuran was added dimethyl 2-oxopropylphosphonate (2.0 g, 12 mmol) dropwise at 0° C. After the addition, the mixture was stirred at 0° C. for 1 hour and p-toluenesulfonyl azide (13% in toluene, 19.2 g, 12.6 mmol) was added dropwise. The mixture was allowed to warm to room temperature and stirred overnight. Water was added and extracted with ethyl acetate (twice). The combined organic layers were washed with brine and concentrated to provide the crude title compound which was used in the next step without purification. MS (DCI/NH3) m/z 193 (M+H)+.

Provenance & Evidence