Trimethylsilylacetylene → (4-Ethylphenylethynyl)trimethylsilane

HRID 1271038Notes

Reaction equation

HRID 1271038 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6](I)=[CH:5][CH:4]=1)[CH3:2].[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12]>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.[Cu](I)I.C(N(CC)CC)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:15]#[C:14][Si:11]([CH3:13])([CH3:12])[CH3:10])=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 1411891-Ethyl-4-iodobenzene

Product 1

HCID 11298629(4-Ethylphenylethynyl)trimethylsilane

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 5.6 mL of 1-ethyl-4-iodobenzene, 75 mL of triethylamine, 6 mL of trimethylsilylacetylene, 0.49 g of dichlorotriphenylphosphine palladium II and 0.314 g copper iodide was magnetically stirred at ambient temperature for 18 hrs. The thick dark brown mixture was filtered, washing the gray precipitate with hexanes. The filtrate and washings were evaporated in vacuo and the residue dissolved in hexanes. This solution was 96.7% pure by GC analysis. The solution was passed down a column of silica gel which had been equilibrated in the same solvent and the eluates evaporated in vacuo to yield 9.3 g of 4-ethyl-1-trimethylsilyl ethynylbenzene as a dark amber liquid.

Workup

  1. filtrationThe thick dark brown mixture was filtered
  2. washwashing the gray precipitate with hexanes
  3. customThe filtrate and washings were evaporated in vacuo
  4. dissolutionthe residue dissolved in hexanes
  5. customthe eluates evaporated in vacuo

Sources & evidence

ORD record
ord-b63a7b74d1b94cfcb24a18afb8bb5c3f
Source dataset
uspto-grants-2007_04
Patent number
US07205297B2

Reaction notes

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