Iodoethane → ethyl ethylphenylphosphinate

HRID 1683660Notes

Reaction equation

HRID 1683660 reaction equation
[H-].[Na+].[C:3]1([PH:9](=[O:13])[O:10][CH2:11][CH3:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:14](I)[CH3:15]>C1COCC1>[CH2:14]([P:9]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)(=[O:13])[O:10][CH2:11][CH3:12])[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178476779HCID 178476779, compound

Product 1

HCID 11008893ethyl ethylphenylphosphinateYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A slurry of sodium hydride (0.13 g of a 60% suspension in mineral oil, 3.2 mmol) in anhydrous THF (10 ml) was treated dropwise with a solution of ethyl phenylphosphinate (0.50 g, 2.9 mmol) over one hour via a syring pump. The mixture was allowed to stir an additional 30 minutes before the addition of ethyl iodide (0.26 ml, 3.2 mmol). After 45 minutes the reaction was quenched with 10% aqueous ammonium chloride (5 ml) and poured into a separatory funnel containing ethyl acetate (50 ml). The organic phase was washed with water, saturated aqueous sodium bicarbonate and brine before being dried over magnesium sulfate, filtered and concentrated to afford 0.30 g (52%) of the title compound as a colorless mobile oil following flash chromatography on silica gel (50% ethyl acetate/hexane); MS: 199 m/z (M+H)+.

Workup

  1. customAfter 45 minutes the reaction was quenched with 10% aqueous ammonium chloride (5 ml)
  2. additionpoured into a separatory funnel
  3. additioncontaining ethyl acetate (50 ml)
  4. washThe organic phase was washed with water, saturated aqueous sodium bicarbonate and brine
  5. dry with materialbefore being dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eeb0d033e567454daedfbb10515d3017
Source dataset
uspto-grants-1997_06
Patent number
US05639732

Reaction notes

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