Trimethylsilylacetylene → 1-Ethynyl-4-pentylbenzene

HRID 1613527

Reaktionsgleichung

Reaktionsgleichung von HRID 1613527
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9](I)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C[Si]([C:17]#[CH:18])(C)C>C(NCC)C.[Cu]I>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:17]#[CH:18])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 1450574-Iodopentylbenzene

Produkt 1

HCID 27751311-Ethynyl-4-pentylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

A mixture of 0.1 mol of 4-pentyliodobenzene, 0.12 mol of trimetylsilylacetylene, 0.0014 mol of bis(triphenylphosphine)-palladium(II) Chloride Pd(PPh3)2Cl2 and 0.7 mmol of copper (I) iodide in 250 ml diethylamine is stirred at room temperature for 20 hours. After evaporation of the solvent the crude product is purified by chromatography on alumina (4:1 petrol/dichloromethane) to give 2-(4-pentylphenyl)-1-trimethylsilyacetylene. Removal of the trimethylsilylgroup is accomplished by treatment this acetylene is methanol with 1 M KOH for 1 hour at room temperature. Evaporation of the methanol and either extraction yields 4-pentylphenylacetylene.

Aufarbeitung

  1. customAfter evaporation of the solvent the crude product
  2. customis purified by chromatography on alumina (4:1 petrol/dichloromethane)
  3. customto give 2-(4-pentylphenyl)-1-trimethylsilyacetylene
  4. customRemoval of the trimethylsilylgroup
  5. customfor 1 hour
  6. customat room temperature
  7. customEvaporation of the methanol
  8. extractioneither extraction

Quellen und Nachweise

ORD-Eintrag
ord-8d3750c7882344f3845bdb3d1508da83
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194178

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