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

HRID 477899

반응식

HRID 477899 반응식
[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

참가 물질

7

반응물 2

HCID 66111TrimethylsilylacetyleneHCID 1400962-Iodo-5-methylthiophene

생성물 1

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

시약·촉매·용매 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 3283Diethyl Ether용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc788479251e400fa5ab1b1dc35ed022
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04889867

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