Sodium hydride → Tetraethyl (phenoxymethylene)-bisphosphonate

HRID 569603Notes

Reaction equation

HRID 569603 reaction equation
[CH2:1]([O:3][P:4]([O-:8])[O:5][CH2:6][CH3:7])[CH3:2].[H-].[Na+].[C:11]1([O:17][CH:18](Cl)Cl)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CN(C)C=O.O>[O:17]([CH:18]([P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])[P:4](=[O:8])([O:5][CH2:6][CH3:7])[O:3][CH2:1][CH3:2])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 319898Dichloromethyl phenyl etherHCID 3780918Diethylphosphite

Product 1

HCID 54483224Tetraethyl (phenoxymethylene)-bisphosphonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Diethylphosphite (20.6 ml) was added dropwise at 20° C. to a stirred suspension of 55% sodium hydride (6.24 g) in dimethylformamide (90 ml). After stirring for a further 15 minutes, the mixture was cooled to 0° C., and dichloromethyl phenyl ether (9.27 g) was added dropwise. Stirring was continued overnight at 45° C., and the mixture was cooled in ice, diluted with water, neutralized and extracted with ethyl acetate. The organic phase was washed repeatedly with water, dried and evaporated in vacuo to yield an oil which was purified by chromatography on silica gel. Eluent: ether-acetone 85:15. The pure title compound was obtained as a colourless oil.

Workup

  1. stirringStirring
  2. waitwas continued overnight at 45° C.
  3. temperaturethe mixture was cooled in ice
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed repeatedly with water
  6. customdried
  7. customevaporated in vacuo
  8. customto yield an oil which
  9. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ddd21daf02a64cb48d14aab9fefdbfa2
Source dataset
uspto-grants-1988_03
Patent number
US04732998

Reaction notes

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