Chloroform → Ethyl 3-oxobutyl(diethoxymethyl)phosphinate

HRID 542298Notes

Reaction equation

HRID 542298 reaction equation
C[Si]([PH:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])([O-:9])[O:6][CH2:7][CH3:8])(C)C.[CH:17]([C:19]([CH3:21])=[O:20])=[CH2:18].C(Cl)(Cl)Cl>O>[O:20]=[C:19]([CH3:21])[CH2:17][CH2:18][P:5]([CH:10]([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])(=[O:9])[O:6][CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 6570Methyl vinyl ketoneHCID 178418659HCID 178418659, compound

Product 1

HCID 14362820Ethyl 3-oxobutyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

The starting material may be prepared as follows: 15.0 g of ethyl trimethylsilyl(diethoxymethyl)phosphonite are added dropwise to a stirred solution of 3.9 g of methyl vinyl ketone under an atmosphere of nitrogen at room temperature. The mixture is then heated to 50° C. for a period of 1 hour. The mixture is then allowed to cool to room temperature, 25 ml of chloroform is then added followed by 10 ml water and this mixture is vigorously stirred for a period of 0.5 h. The organic layer is then separated, dried over magnesium sulphate and concentrated under reduced pressure and the crude product distilled under reduced pressure to give ethyl 3-oxobutyl(diethoxymethyl)phosphinate, b.p. 130°-135° C./0.02 mbar, 31P=+45.3 ppm (CDCl3).

Workup

  1. customThe starting material may be prepared
  2. temperatureto cool to room temperature
  3. customThe organic layer is then separated
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. distillationthe crude product distilled under reduced pressure

Sources & evidence

ORD record
ord-62201ce4b5144577b582e64f41a03265
Source dataset
uspto-grants-1987_04
Patent number
US04656298

Reaction notes

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