Water → HCID 53895791, compound

HRID 1369277Notes

Reaction equation

HRID 1369277 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=C)=[C:8]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1.[OH2:23]>C(Cl)(Cl)(Cl)Cl.CC#N.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:23])=[C:8]([P:14]([O:19][CH2:20][CH3:21])([O:16][CH2:17][CH3:18])=[O:15])[CH:7]=1

Participants

6

Reactant 2

HCID 962WaterHCID 54570789HCID 54570789, compound

Product 1

HCID 53895791HCID 53895791, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 5943Carbon TetrachlorideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

3-(3-Diethoxyphosphoryl-4-vinyl-phenyl)propionic acid methyl ester (200 mg, 0.61 mmol) was dissolved in 3.9 mL CCl4 and 3.9 mL of MeCN. NaIO4 (388 mg, 1.81 mmol) was dissolved in 6 mL H2O and was added. The mixture was stirred vigorously and RuCl3 (10 mg, 0.05 mmol) was then added and the mixture was stirred for 1 hr at rt The reaction was diluted with DCM, organic layer was separated, dried Na2SO4 and concentrated. The residue was purified by flash column chromatography on silica gel (4/1 EtOAc/hexane, Rf=0.37) to give pure product as an oil, 153 mg (yield 76%).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 1 hr at rt The reaction
  3. customwas separated
  4. concentrationdried Na2SO4 and concentrated
  5. customThe residue was purified by flash column chromatography on silica gel (4/1 EtOAc/hexane, Rf=0.37)
  6. customto give pure product as an oil, 153 mg (yield 76%)

Sources & evidence

ORD record
ord-0fd4cb04004e4a339aee0e4e315192e4
Source dataset
uspto-grants-2003_06
Patent number
US06576766B1

Reaction notes

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