Water → 1,2-Bis(4-methoxyphenyl)ethyne

HRID 1760090

Reaktionsgleichung

Reaktionsgleichung von HRID 1760090
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)#[CH:2].I[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.C(NC(C)C)(C)C.O>C1COCC1.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>[CH3:10][O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:4][CH:5]=1

Komponenten

8

Edukt 4

HCID 962WaterHCID 7912DiisopropylamineHCID 696764-IodoanisoleHCID 2510201-Ethynyl-4-methoxybenzene

Produkt 1

HCID 6172341,2-Bis(4-methoxyphenyl)ethyneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-ethynylanisole (700 mg, 5.30 mmol), 4-iodoanisole (1.30 g, 5.55 mmol), (PPh3)2PdCl2 (74.4 mg, 0.106 mmol), and CuI (10.1 mg, 0.053 mmol) in THF (7 ml), diisopropyl amine (1.13 g, 11.1 mmol) was added dropwise under ice cooling under argon atmosphere. After stirring at room temperature for 1 h, water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with water then saturated brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=15/1) to give bis(4-methoxyphenyl)ethyne (95%).

Aufarbeitung

  1. additionwas added dropwise under ice cooling under argon atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialsaturated brine, dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=15/1)

Quellen und Nachweise

ORD-Eintrag
ord-8e354f6f47b9491e8ee9038da2c0a51a
Quelldatensatz
uspto-grants-2005_01
Patentnummer
US06838574B1

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