Chlorotrimethylsilane → 4-[Hydroxy-(4-phenylbutyl)phosphinyl]-4,4-dimethyl-2-butanone

HRID 1981865Notes

Reaction equation

HRID 1981865 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.[O:26]=[C:27]([CH:29]=[C:30]([CH3:32])[CH3:31])[CH3:28]>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)([C:30]([CH3:32])([CH3:31])[CH2:29][C:27](=[O:26])[CH3:28])=[O:13]

Participants

6

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 8858Mesityl oxideHCID 132746654-Phenylbutylphosphonous acid

Product 1

HCID 133599054-[Hydroxy-(4-phenylbutyl)phosphinyl]-4,4-dimethyl-2-butanoneYield 37.8%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 4-phenylbutyl phosphonous acid (0.5 g, 0.0025 mole) in chloroform (15 ml) was added triethylamine (0.77 ml, 0.005 mole), trimethyl silylchloride (0.70 ml, 0.005 mole) and mesityl oxide (0.32 ml, 0.0025 mole). The reaction mixture was stirred at reflux temperature for 18 hours. CHCl3 was removed in vacuo. The residue was diluted with ether and washed with 5% aqueous NaHCO3 solution. The aqueous layer was acidified with concentrated HCl and extracted twice with ether and once with EtOAc. Organic layers were combined and extracted with brine, dried over Na2SO4 and solvent was removed to give 0.28 g of the product an an oil.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customCHCl3 was removed in vacuo
  3. additionThe residue was diluted with ether
  4. washwashed with 5% aqueous NaHCO3 solution
  5. extractionextracted twice with ether and once with EtOAc
  6. extractionextracted with brine
  7. dry with materialdried over Na2SO4 and solvent
  8. customwas removed

Sources & evidence

ORD record
ord-31f892cac8c64ddc89b0646e3a46c61c
Source dataset
uspto-grants-1986_06
Patent number
US04594199

Reaction notes

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