Sodium hydride → (1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

HRID 659130Notes

Reaction equation

HRID 659130 reaction equation
[H-].[Na+].[O:3]=[C:4]([CH3:12])[CH2:5][P:6](=[O:11])([O:9][CH3:10])[O:7][CH3:8].C(NC1C=CC(S([N:26]=[N+:27]=[N-])(=O)=O)=CC=1)(=O)C>C1C=CC=CC=1.C1COCC1>[N+:26](=[C:5]([P:6](=[O:11])([O:9][CH3:10])[O:7][CH3:8])[C:4](=[O:3])[CH3:12])=[N-:27]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 77872Dimethyl (2-oxopropyl)phosphonate2×HCID 51291854-Acetamidobenzenesulfonyl azide2×

Product 1

HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-oneYield 100.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent3×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
7.5 °C

Procedure

To a suspension of 4.1 g of NaH (washed with hexane) in 110 mL of benzene and 25 mL of THF at 5° C., was added 15.5 g of dimethyl 2-oxopropylphosphonate (Formula 13) in 15 mL of benzene. The resulting solution was stirred at 5-10° C. for 1 hour. A solution of 24.7 g of 4-acetamidobenzenesulfonyl azide (Formula 14) in 25 mL of benzene and 50 mL of THF was then added and the mixture was stirred at room temperature for 2 hours. The yellow suspension was filtered through celite and washed with ethyl ether. The filtrate was concentrated to give 18 g of dimethyl 1-diazo-2-oxopropylphosphonate (Formula 15) as a light yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. filtrationThe yellow suspension was filtered through celite
  3. washwashed with ethyl ether
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-ae16b57cc819488582d151f102a18921
Source dataset
uspto-grants-2011_12
Patent number
US08080570B2

Reaction notes

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