Acetic Acid → HCID 10330332, compound

HRID 865849Notes

Reaction equation

HRID 865849 reaction equation
[Na].[F:2][CH:3]([F:9])[PH:4](=[O:8])[O:5][CH2:6][CH3:7].[C:10](#[N:12])[CH3:11].[C:13](O)(=O)C>C(O)C>[C:10]([CH2:11][CH2:13][P:4]([CH:3]([F:9])[F:2])(=[O:8])[O:5][CH2:6][CH3:7])#[N:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 5360545SodiumHCID 178476821HCID 178476821, compound

Product 1

HCID 10330332HCID 10330332, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

660 mg (28.8 mmol) of sodium are dissolved in 40 ml of ethanol. The solution is cooled to -10° and 8.6 g (57.6 mmol) of ethyl P-difluoromethylphosphinate and 3.8 ml (57.6 mmol) of acetonitrile are added with stirring. The reaction mixture is then allowed to warm up to room temperature and stirred for additional 17 hours and then adjusted to pH 6 by addition of glacial acetic acid. The solvents are evaporated and the residue is dissolved in dichloromethane, washed twice with water, dried over magnesium sulphate and evaporated to dryness. The crude product is purified by chromatography on silica gel with ethyl acetate/dichloromethane (7:3) as eluent. The fractions containing the desired product are combined and evaporated to dryness yielding ethyl P-(2-cyanoethyl)-P-difluoromethyl-phosphinate as an oil of Rf =0.54 (above eluent).

Workup

  1. temperatureThe solution is cooled to -10°
  2. stirringstirred for additional 17 hours
  3. customThe solvents are evaporated
  4. dissolutionthe residue is dissolved in dichloromethane
  5. washwashed twice with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated to dryness
  8. customThe crude product is purified by chromatography on silica gel with ethyl acetate/dichloromethane (7:3) as eluent
  9. additionThe fractions containing the desired product
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-dd6ce0cd49564382add27c47925cea13
Source dataset
uspto-grants-1996_10
Patent number
US05567840

Reaction notes

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