Hydrochloric Acid → HCID 13359897, compound

HRID 1981861Notes

Reaction equation

HRID 1981861 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11]([O-:15])[O:12][CH2:13][CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C[Si](Cl)(C)C.[C:28](#[N:31])[CH:29]=[CH2:30].Cl>C(Cl)(Cl)Cl>[CH2:13]([O:12][P:11]([CH2:10][CH2:9][CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([CH2:30][CH2:29][C:28]#[N:31])=[O:15])[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 7855AcrylonitrileHCID 8471TriethylamineHCID 86740835HCID 86740835, compound

Product 1

HCID 13359897HCID 13359897, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-phenylbutyl phosphonous acid, ethyl ester (0.5 g, 0.0022 mole) in chloroform (10 ml) was added triethylamine (0.341 ml, 0.0024 mole), trimethyl silylchloride (0.303 ml, 0.0024 mole) and acrylonitrile (0.17 ml, 0.0024 mole). The reaction mixture was stirred at reflux temperature for 18 hours; the mixture was poured into crushed ice (15 gm) containing 10 ml 10% HCl acid. It was shaken in a separatory funnel; a chloroform layer was evaporated, and the aqueous layer extracted once with ethyl acetate. The combined organic phase was washed with water, dried over anhydrous sodium sulphate and the organic solvent removed on a rotavap to produce the title compound as a thick oil (0.6 g, 97% yield).

Workup

  1. temperatureat reflux temperature for 18 hours
  2. additionthe mixture was poured
  3. stirringIt was shaken in a separatory funnel
  4. customa chloroform layer was evaporated
  5. extractionthe aqueous layer extracted once with ethyl acetate
  6. washThe combined organic phase was washed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. customthe organic solvent removed on a rotavap

Sources & evidence

ORD record
ord-32dc1353fde0408e97ee10428cf9b82d
Source dataset
uspto-grants-1986_06
Patent number
US04594199

Reaction notes

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