Toluene → 4-[(4-Pentylphenyl)ethynyl]phenol

HRID 1057261

Reaktionsgleichung

Reaktionsgleichung von HRID 1057261
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[CH:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C([O:17][C:18]1[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=1)(=O)C.C1(C)C=CC=CC=1>C(NC(C)C)(C)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)I>[CH2:1]([C:6]1[CH:7]=[CH:8][C:9]([C:12]#[C:13][C:21]2[CH:20]=[CH:19][C:18]([OH:17])=[CH:23][CH:22]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Komponenten

7

Edukt 3

HCID 1140TolueneHCID 1417934-IodophenylacetateHCID 27751311-Ethynyl-4-pentylbenzene

Produkt 1

HCID 186711384-[(4-Pentylphenyl)ethynyl]phenol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 7912DiisopropylamineLösungsmittel

Versuchsvorschrift

4-Pentylphenylacetylene (10.5 g, 61.4 mmol), 4-acetoxyphenyl iodide (16.1 g, 61.4 mmol), a catalytic amount of Pd(PPh3)2Cl2 and a catalytic amount of copper iodide were stirred in diisopropylamine (100 ml) at 70° C. After 5 minutes, a precipitate was seen and the mixture became unstirrable, toluene (100 ml) was added. The mixture was stirred at room temperature for 24 hours and then evaporated to dryness on a rotary evaporator. The residue was redissolved in aqueous potassium hydroxide ethanolic solution and stirred at 70° C. overnight. The mixture was evaporated to dryness, then partitioned between ethyl acetate and water, the organic phase was removed, dried and evaporated. The residue was purified by flash column chromatography using DCM as eluant. A pink coloured solid was left after evaporation of the appropriate fractions. Yield=10.4 g, 64%. 1H-NMR and IR spectroscopy gave the expected signals.

Aufarbeitung

  1. customevaporated to dryness on a rotary evaporator
  2. dissolutionThe residue was redissolved in aqueous potassium hydroxide ethanolic solution
  3. stirringstirred at 70° C. overnight
  4. customThe mixture was evaporated to dryness
  5. custompartitioned between ethyl acetate and water
  6. customthe organic phase was removed
  7. customdried
  8. customevaporated
  9. customThe residue was purified by flash column chromatography
  10. waitA pink coloured solid was left
  11. customafter evaporation of the appropriate fractions
  12. custom1H-NMR and IR spectroscopy gave the expected signals

Quellen und Nachweise

ORD-Eintrag
ord-fbc96aea378f44dca8347db3b9ca696d
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514578B1

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