Reaktion #609394

Reaktionsgleichung

p-toluenesulfonyl azide

dimethyl 2-oxopropylphosphonate

sodium hydride

benzene tetrahydrofuran

→

crude title compound

dimethyl 1-diazo-2-oxopropylphosphonate

Lösungsmittel

Water

—

6/1

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturto warm to room temperature
3. 3
   workup.STIRRINGstirred overnight
4. 4
   Extraktionextracted with ethyl acetate (twice)
5. 5
   WaschenThe combined organic layers were washed with brine
6. 6
   Einengenconcentrated

Vorschrift

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)+.

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