Acetic Acid → Ethyl 2-cyanopropyl(diethoxymethyl)phosphinate

HRID 542296

Reaction equation

HRID 542296 reaction equation
[CH2:1]([O:3][P:4]([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])[O-:5])[CH3:2].[C:13](#[N:17])[C:14]([CH3:16])=[CH2:15].[H-].[Na+].C(O)(=O)C>C(O)C>[CH2:1]([O:3][P:4]([CH2:15][CH:14]([C:13]#[N:17])[CH3:16])([CH:6]([O:10][CH2:11][CH3:12])[O:7][CH2:8][CH3:9])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 31368MethacrylonitrileHCID 85631043Ethyl(diethoxymethyl)phophonite

Product 1

HCID 14362815Ethyl 2-cyanopropyl(diethoxymethyl)phosphinate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

The starting material may be prepared as follows: A solution of 23.5 g of ethyl(diethoxymethyl)phosphonite and 6.7 g of methacrylonitrile in 30 ml of ethanol is added dropwise to a stirred mixture of 1.2 g of sodium hydride (50% dispersion in oil) in 30 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 under reduced pressure to give ethyl-2-cyanopropyl(diethoxymethyl)phosphinate, b.p. 116° C./0.01 mbar, 31P=+40.4 and +40.3 ppm (CDCl3).

Workup

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

Sources & evidence

ORD record
ord-bb9103e32fe2431a91d4f1cf01b957d5
Source dataset
uspto-grants-1987_04
Patent number
US04656298

Linked notes

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