Iodoethane → Tetraethyl (1-phenoxypropylidene)-bisphosphonate

HRID 569616Notes

Reaction equation

HRID 569616 reaction equation
[O:1]([CH:8]([P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])[P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:27](I)[CH3:28]>CN(C)C=O.C(OCC)(=O)C>[O:1]([C:8]([P:17](=[O:24])([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20])([P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])[CH2:27][CH3:28])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 54483224Tetraethyl (phenoxymethylene)-bisphosphonate

Product 1

HCID 53742288Tetraethyl (1-phenoxypropylidene)-bisphosphonate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Tetraethyl (phenoxymethylene)-bisphosphonate (1.14 g) was added to a suspension of 55% sodium hydride (0.15 g) in dimethylformamide (10 ml). After 45 minutes at room temperature, ethyl iodide (0.49 ml) was added, and the mixture was left overnight at room temperature, diluted with ethyl acetate and washed with 40% aqueous calcium chloride. The organic phase was dried and evaporated to leave an oil which was purified by chromatography on silica gel. The title compound was isolated as a colourless oil.

Workup

  1. waitthe mixture was left overnight at room temperature
  2. washwashed with 40% aqueous calcium chloride
  3. customThe organic phase was dried
  4. customevaporated
  5. customto leave an oil which
  6. customwas purified by chromatography on silica gel

Sources & evidence

ORD record
ord-d3e6e6ed0a0a4afe9c17dd9befff510f
Source dataset
uspto-grants-1988_03
Patent number
US04732998

Reaction notes

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