Trimethylsilylacetylene → HCID 69915703, compound

HRID 1840692Notes

Reaction equation

HRID 1840692 reaction equation
I[C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17]>[Cu](I)I.CN(C)C>[CH3:15][Si:16]([CH3:18])([CH3:17])[C:19]#[C:20][C:3]1[C:4]2[CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:12]=2[CH:13]=[CH:14][CH:2]=1

Participants

5

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 2240942-Iodo-9H-fluorene

Product 1

HCID 69915703HCID 69915703, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 1146TrimethylamineSolvent

Procedure

Thereafter, to 150 ml of trimethylamine were added 7.89 g of 2-iodofluorene, 379 mg (0.54 mmol) of bis[triphenylphosphine]palladium dichloride and 51 mg (0.27 mmol) of copper iodide. 4.2 ml (29.7 mmol) of trimethylsilylacetylene was added slowly to the reaction mixture. After the reaction was stirred for 8 h at room temperature, solvent was removed under reduced pressure. The residue was extracted with benzene and the benzene layer was washed with distilled water. The washed benzene layer was concentrated to give 6.02 g (85%) of 2-trimethylsilylethynyl fluorene.

Workup

  1. customsolvent was removed under reduced pressure
  2. extractionThe residue was extracted with benzene
  3. washthe benzene layer was washed with distilled water
  4. concentrationThe washed benzene layer was concentrated

Sources & evidence

ORD record
ord-ecde6133bf4441e6bf0837a032dc3328
Source dataset
uspto-grants-2004_01
Patent number
US06682782B2

Reaction notes

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