Sodium Azide → Diethyl 3-(2-(2-azidoethoxy)ethoxy)-1,1-difluoropropylphosphonate

HRID 2204951Notes

Reaction equation

HRID 2204951 reaction equation
[F:1][C:2]([P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])([F:12])[CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10]I.[N-:21]=[N+:22]=[N-:23].[Na+]>CN(C=O)C.C(OCC)(=O)C>[N:21]([CH2:10][CH2:9][O:8][CH2:7][CH2:6][O:5][CH2:4][CH2:3][C:2]([P:13](=[O:20])([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])([F:12])[F:1])=[N+:22]=[N-:23]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 58166512Diethyl 1,1-difluoro-3-(2-(2-iodoethoxy)ethoxy)propylphosphonate

Product 1

HCID 86678262Diethyl 3-(2-(2-azidoethoxy)ethoxy)-1,1-difluoropropylphosphonate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diethyl 1,1-difluoro-3-(2-(2-iodoethoxy)ethoxy)propylphosphonate (1 eq) in DMF (0.5 M) was added sodium azide (3 eq). The reaction mixture was stirred at room temperature for 90 minutes. The mixture was diluted with ethyl acetate, and washed with water. The aqueous phases were back extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, and concentrated en vaccuo. The crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 10-50% EtOAc/Hex to give the product as a yellowish oil.

Workup

  1. washwashed with water
  2. extractionThe aqueous phases were back extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated en vaccuo
  6. customThe crude mixture was purified by flash chromatography on a COMBIFLASH® system (ISCO)

Sources & evidence

ORD record
ord-755c5f2675e44188a6bacc66028ca4a6
Source dataset
uspto-grants-2016_06
Patent number
US09365506B2

Reaction notes

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