Allyl Alcohol → HCID 18510217, compound

HRID 1371025Notes

Reaction equation

HRID 1371025 reaction equation
[F:1][C:2]([F:18])([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][CH:4]=1.[CH2:19]([OH:22])[CH:20]=[CH2:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C=O)C.O.C([O-])(=O)C.[Ag+].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:1][C:2]([F:18])([P:10](=[O:17])([O:14][CH2:15][CH3:16])[O:11][CH2:12][CH3:13])[C:3]1[CH:8]=[CH:7][C:6](/[CH:21]=[CH:20]/[CH2:19][OH:22])=[CH:5][CH:4]=1

Participants

8

Reactant 3

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 10872827HCID 10872827, compound

Product 1

HCID 18510217HCID 18510217, compound

Reagents, catalysts & solvents 4

HCID 11246Silver acetateCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of diethyl difluoro(4-iodophenyl)methylphosphonate T. R. Burke Tetrahedron Letters, 551,1994, (2.50 g, 6.91 mmol) in DMF (25 ml) was added allyl alcohol (1.3 ml), silver acetate (1.1 g), palladium acetate (0.075 g), and triphenyl phosphine (0.175 g). The reaction mixture was refluxed for 2 hours. After cooling to room temperature the reaction was diluted with water and extracted with ethyl acetate. The mixture was filtered through a pad of celite. The organic layer was separated and washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified using flash chromatography with hexane/ethyl acetate 75% to give 0.6 g of the title compound.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. extractionextracted with ethyl acetate
  3. filtrationThe mixture was filtered through a pad of celite
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-5bb11c73890b4425a0250003e75d59a0
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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