Triphenylphosphine → HCID 13656008, compound

HRID 745904Notes

Reaction equation

HRID 745904 reaction equation
I/[CH:2]=[C:3]1\[CH2:4][CH2:5][C:6](=[O:8])[O:7]\1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:28][Si:29]([CH3:31])([CH3:30])[C:32]#[C:33]/[CH:2]=[C:3]1\[CH2:4][CH2:5][C:6](=[O:8])[O:7]\1

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 13351341HCID 13351341, compound

Product 1

HCID 13656008HCID 13656008, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 5(E)-iodomethylidenetetrahydro-2-furanone (820 mg), palladium (II) acetate (40 mg) and triphenylphosphine (80 mg) in 5 ml of triethylamine under argon was added 42 ml of trimethylsilylacetylene. The solution was refluxed for 4 hours and then partitioned between 150 ml of methylene chloride and 50 ml of water. The methylene chloride layer, dried over magnesium sulphate, was evaporated to an oil. This oil was purified by column chromatography on silica gel (10% ethyl acetate:petrolium ether, IR: 2130, 1820, 1762 cm-1.

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. custompartitioned between 150 ml of methylene chloride and 50 ml of water
  3. dry with materialThe methylene chloride layer, dried over magnesium sulphate
  4. customwas evaporated to an oil
  5. customThis oil was purified by column chromatography on silica gel (10% ethyl acetate

Sources & evidence

ORD record
ord-23fe3cd158d442eab0bbc8e2ce23c914
Source dataset
uspto-grants-1986_07
Patent number
US04602006

Reaction notes

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