Trimethylsilylacetylene → (5-Methyl-2-thienylethynyl)trimethylsilane

HRID 2232391

Reaction equation

HRID 2232391 reaction equation
[CH3:1][Si:2]([C:5]#[CH:6])([CH3:4])[CH3:3].I[C:8]1[S:9][C:10]([CH3:13])=[CH:11][CH:12]=1>C(N(CC)CC)C.C(OCC)C.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>[CH3:1][Si:2]([CH3:4])([CH3:3])[C:5]#[C:6][C:8]1[S:9][C:10]([CH3:13])=[CH:11][CH:12]=1

Participants

7

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 1400962-Iodo-5-methylthiophene

Product 1

HCID 14643579(5-Methyl-2-thienylethynyl)trimethylsilaneYield 92.6%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

Under a dry nitrogen atmosphere 3.0 grams (0.031 mole) of trimethylsilylacetylene was added to a stirred mixture of 5.5 grams (0.025 mole) of 2-iodo-5-methylthiophene in 50 ml of triethylamine. To this mixture was added approximately 0.05 gram of dichlorobis(triphenylphosphine)palladium (II) and approximately 0.05 gram of copper (I) iodide. The resultant mixture was stirred at room temperature for approximately 18 hours. The triethylamine was removed from the mixture by evaporation under reduced pressure leaving a residue. This residue was dissolved in diethyl ether and the resultant solution was washed in succession with an aqueous, 10% ammonium chloride solution, water, and an aqueous, saturated sodium chloride solution. The washed organic solution was dried over anhydrous sodium sulfate and was filtered. The filtrate was evaporated under reduced pressure leaving a residue. This residue was purified by column chromatography on silica gel, eluting with n-hexane, to yield 4.5 grams of 1-trimethylsilyl-2-(5-methylthien-2-yl)ethyne as an oil.

Workup

  1. customThe triethylamine was removed from the mixture by evaporation under reduced pressure
  2. customleaving a residue
  3. washthe resultant solution was washed in succession with an aqueous, 10% ammonium chloride solution, water
  4. dry with materialThe washed organic solution was dried over anhydrous sodium sulfate
  5. filtrationwas filtered
  6. customThe filtrate was evaporated under reduced pressure
  7. customleaving a residue
  8. customThis residue was purified by column chromatography on silica gel
  9. washeluting with n-hexane

Sources & evidence

ORD record
ord-665f763b6cd64fbdabbccb506c1f9b96
Source dataset
uspto-grants-1988_11
Patent number
US04788207

Linked notes

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