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

HRID 1784118Notes

Reaction equation

HRID 1784118 reaction equation
[H-].[Na+].CS(N=[N+:8]=[N-:9])(=O)=O.CS(Cl)(=O)=O.[N-]=[N+]=[N-].[Na+].[CH3:19][O:20][P:21]([CH2:25][C:26](=[O:28])[CH3:27])(=[O:24])[O:22][CH3:23]>C1(C)C=CC=CC=1.O1CCCC1>[CH3:19][O:20][P:21]([C:25](=[N+:8]=[N-:9])[C:26](=[O:28])[CH3:27])(=[O:24])[O:22][CH3:23]

Participants

8

Reactant 5

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 77872Dimethyl (2-oxopropyl)phosphonateHCID 556271Methanesulfonyl azide

Product 1

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

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of sodium hydride in dry toluene, (2-oxo-propyl)-phosphonic acid dimethyl ester was added slowly. The solution mixture was stirred for 1 hour. Methanesulfonyl azide, prepared by the reaction of methanesulfonyl chloride and sodium azide, dissolved in dry toluene and dry tetrahydrofuran was added to a solution. The mixture was allowed to slowly warm up to the ambient temperature and stirred for additional 2 hours. Filtration through a celite filter cake gave yellowish oil of (1-Diazo-2-oxo-propyl)-phosphonic acid dimethyl ester, which was used for the next step without any further purification.

Workup

  1. additionwas added slowly
  2. stirringstirred for additional 2 hours
  3. filtrationFiltration through a celite
  4. filtrationfilter cake

Sources & evidence

ORD record
ord-6548c61644844463a0b82f95a1cc807e
Source dataset
uspto-grants-2009_03
Patent number
US07501529B2

Reaction notes

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