Chlorotrimethylsilane → HCID 13359895, compound

HRID 1981867Notes

Reaction equation

HRID 1981867 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][P:11]([OH:13])[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.C[Si](Cl)(C)C.[C:26]([O:30][CH3:31])(=[O:29])[CH:27]=[CH2:28]>C(Cl)(Cl)Cl>[OH: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)([CH2:28][CH2:27][C:26]([O:30][CH3:31])=[O:29])=[O:13]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 132746654-Phenylbutylphosphonous acid

Product 1

HCID 13359895HCID 13359895, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-phenylbutyl phosphonous acid (1 g, 0.005 mole) in chloroform (40 ml) was added triethylamine (1.55 ml, 0.0111 mole), trimethyl silylchloride (1.41 ml, 0.0111 mole) and methyl acrylate (0.50 ml, 0.0055 mole). The reaction mixture was stirred at reflux for 18 hours. CHCl3 was removed in vacuo. The residue was diluted with ether and extracted with 5% aqueous NaHCO3 solution. Aqueous layers were acidified with concentrated HCl and extracted with ether. Organic layers were extracted with brine and dried over Na2SO4. Solvent was removed in vacuo to give 1.26 g of an oil. T-60 1H NMR appeared to characterize product from Michael addition.

Workup

  1. temperatureat reflux for 18 hours
  2. customCHCl3 was removed in vacuo
  3. additionThe residue was diluted with ether
  4. extractionextracted with 5% aqueous NaHCO3 solution
  5. extractionextracted with ether
  6. extractionOrganic layers were extracted with brine
  7. dry with materialdried over Na2SO4
  8. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-ef216d258bb44357a57650736adec19c
Source dataset
uspto-grants-1986_06
Patent number
US04594199

Reaction notes

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