Acetic Acid → isobutyl P-(3-cyanoprop-2-yl)-P-methyl-phosphinate

HRID 2210764Notes

Reaction equation

HRID 2210764 reaction equation
[CH3:1][P:2]([O-:8])[O:3][CH2:4][CH:5]([CH3:7])[CH3:6].[C:9](#[N:13])/[CH:10]=[CH:11]/[CH3:12].[H-].[Na+].C(O)(=O)C>C(O)C>[C:9]([CH2:10][CH:11]([P:2]([CH3:1])(=[O:8])[O:3][CH2:4][CH:5]([CH3:7])[CH3:6])[CH3:12])#[N:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 637921CrotononitrileHCID 86741778Isobutyl methanephosphonite

Product 1

HCID 23374761isobutyl P-(3-cyanoprop-2-yl)-P-methyl-phosphinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 50.0 g of isobutyl P-methylphosphonite and 22.8 g of crotononitrile in 50 ml of dry ethanol is added to a stirred mixture of 0.8 g of sodium hydride (50% dispersion in oil) in 25 ml of ethanol at 0° C. , under an atmosphere of nitrogen. The reaction mixture is allowed to warm to room temperature and stirred for 4 hours. 1 ml of glacial acetic acid is added and the mixture is concentrated under reduced pressure. The resulting crude product is dissolved in 50 ml of ethyl acetate, washed twice with 25 ml of water, and the organic extract is dried over magnesium sulphate, and then concentrated under reduced pressure. The crude product is distilled to give isobutyl P-(3-cyanoprop-2-yl)-P-(methyl)phosphinate, b.p. 110°/0.125 mbar, 31P-NMR spectrum: δ=+55.9 and +55.5 ppm (CDCl3).

Workup

  1. concentrationthe mixture is concentrated under reduced pressure
  2. dissolutionThe resulting crude product is dissolved in 50 ml of ethyl acetate
  3. washwashed twice with 25 ml of water
  4. extractionthe organic extract
  5. dry with materialis dried over magnesium sulphate
  6. concentrationconcentrated under reduced pressure
  7. distillationThe crude product is distilled

Sources & evidence

ORD record
ord-cdaaa006f1cb48c7ba91abc56a210ef7
Source dataset
uspto-grants-1995_10
Patent number
US05461040

Reaction notes

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