Hydrochloric Acid → HCID 13359898, compound

HRID 1981860Notes

Reaction equation

HRID 1981860 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]([OH:32])(=[O: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]([OH:32])=[O:31])=[O:15])[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 6581Acrylic AcidHCID 8471TriethylamineHCID 86740835HCID 86740835, compound

Product 1

HCID 13359898HCID 13359898, compoundYield 61%

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 (0.68 ml, 0.0049 mole), trimethyl silylchloride (0.61 ml, 0.0049 mole) and acrylic acid (0.175 g, 0.0024 mole). The reaction mixture was stirred at room 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 20 ml chloroform. The combined organic phase was washed with water and sodium bicarbonate, dried over anhydrous sodium sulfate and the organic solvent removed on a rotavap to produce the title compound as a thick oil (0.4 g, 61% yield).

Workup

  1. additionthe mixture was poured
  2. stirringIt was shaken in a separatory funnel
  3. customa chloroform layer was evaporated
  4. extractionthe aqueous layer extracted once with 20 ml chloroform
  5. washThe combined organic phase was washed with water and sodium bicarbonate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe organic solvent removed on a rotavap

Sources & evidence

ORD record
ord-ee50bfdff6d848b7a1921ebdfb744ea5
Source dataset
uspto-grants-1986_06
Patent number
US04594199

Reaction notes

Loading…