Trimethylsilylacetylene → HCID 58047045, compound

HRID 1888748Notes

Reaction equation

HRID 1888748 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.C1COCC1.C(N(CC)CC)C.[CH3:25][Si:26]([C:29]#[CH:30])([CH3:28])[CH3:27]>C(OCC)(=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:30]#[C:29][Si:26]([CH3:28])([CH3:27])[CH3:25])=[CH:8][CH:7]=2)[CH2:3][CH2:2]1

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 226767311-(Cyclopropylmethoxy)-4-iodobenzeneHCID 68616177Triethylamine tetrahydrofuran

Product 1

HCID 58047045HCID 58047045, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(cyclopropylmethoxy)-4-iodobenzene (2.49 g, 9.09 mmol) and copper(I) iodide (86.6 mg, 0.455 mmol) in a mixed solvent of THF-triethylamine (8 mL-2 mL) was added bis(triphenylphosphine)palladium(II) chloride (319 mg, 0.455 mmol), and the mixture was deaerated. Trimethylsilylacetylene (1.54 mL, 10.9 mmol) was added dropwise thereto, and the mixture was stirred under a nitrogen atmosphere for 30 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solution was purified by basic silica gel column chromatography (ethyl acetate), and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=9:1) to give the title compound (1.52 g, yield 69%) as an oil.

Workup

  1. washthe mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solution was purified by basic silica gel column chromatography (ethyl acetate)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-91cfa1aa026d4e6e8617c59c02f91972
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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