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

HRID 522212Notes

Reaction equation

HRID 522212 reaction equation
[H-].[Na+].C1C=CC=CC=1.O1CCCC1.[O:14]=[C:15]([CH3:23])[CH2:16][P:17](=[O:22])([O:20][CH3:21])[O:18][CH3:19].C1(C)C=CC(S([N:33]=[N+:34]=[N-])(=O)=O)=CC=1>O>[N+:33](=[C:16]([P:17](=[O:22])([O:20][CH3:21])[O:18][CH3:19])[C:15](=[O:14])[CH3:23])=[N-:34]

Participants

6

Reactant 4

HCID 13661p-Toluenesulfonyl azideHCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 22633675Benzene tetrahydrofuran

Product 1

HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  1. additionAfter the addition
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. extractionextracted with ethyl acetate (twice)
  5. washThe combined organic layers were washed with brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e055d7e5dfd48e7b8a87a1b8bf782f4
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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