Chloromethyl Methyl Ether → Diethyl 1-(methoxymethyl)-2,5-dioxo-4-imidazolylphosphonate

HRID 1648513Notes

Reaction equation

HRID 1648513 reaction equation
[O:1]=[C:2]1[N:6]=[C:5]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[C:4](=[O:15])[NH:3]1.[H-].[Na+].[CH3:18][O:19][CH2:20]Cl>CN(C=O)C.CCOCC.C(OCC)(=O)C>[CH3:18][O:19][CH2:20][N:3]1[C:4](=[O:15])[C:5]([P:7](=[O:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])=[N:6][C:2]1=[O:1]

Participants

7

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 53733419Diethyl (2,5-dioxo-2,5-dihydro-1H-imidazol-4-yl)phosphonate

Product 1

HCID 53791991Diethyl 1-(methoxymethyl)-2,5-dioxo-4-imidazolylphosphonate

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 2,5-dioxo-4-imidazolylphosphonate (3.61 g, 0.015 moles) in DMF (10 mL), under N2,is added sodium hydride (80% dispersion in oil) (0.55 g, 0.018 moles) and stirred for 5 minutes. Chloromethyl methyl ether (tech. grade 85%) (1.9 mL, 0.021 moles) is added. This mixture is stirred at room temperature for 4 hours, diluted with ether and ethyl acetate (300 mL) and then washed with water and brine before drying over MgSO4. The aqueous layer is back extracted with methylene chloride and combined with the previous organic fraction. Evaporation of solvents and chromatography (eluant 1% methanol in chloroform) and evaporation under high vacuum affords the required product. MS (EI) 280

Workup

  1. stirringThis mixture is stirred at room temperature for 4 hours
  2. washwashed with water and brine
  3. dry with materialbefore drying over MgSO4
  4. extractionThe aqueous layer is back extracted with methylene chloride
  5. customEvaporation of solvents and chromatography (eluant 1% methanol in chloroform) and evaporation under high vacuum

Sources & evidence

ORD record
ord-89a80d5b31b54b32b10691d2a7103986
Source dataset
uspto-grants-1995_07
Patent number
US05436260

Reaction notes

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