Trimethylsilylacetylene → Benzenamine, N,N-dibutyl-4-[(trimethylsilyl)ethynyl]-

HRID 2369631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369631
I[C:2]1[CH:16]=[CH:15][C:5]([N:6]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>CCN(CC)CC.C1C=CC=CC=1.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>[CH3:17][Si:18]([C:21]#[C:22][C:2]1[CH:16]=[CH:15][C:5]([N:6]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:7][CH2:8][CH2:9][CH3:10])=[CH:4][CH:3]=1)([CH3:20])[CH3:19]

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 13169159N,N-Dibutyl-4-iodoaniline

Produkt 1

HCID 12079525Benzenamine, N,N-dibutyl-4-[(trimethylsilyl)ethynyl]-Ausbeute 82,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 241BenzeneLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Cuprous iodide (23 mg, 1 mol %) was added to 4-iodo-N,N-dibutylaniline (4 g, 12.1 mmol), trimethylsilylacetylene (2.37 g, 24.2 mmol) and Pd(PPh3)2Cl2 (84 mg, 1 mol %) in dry Et3N (40 mL) under nitrogen. The resulting solution was stirred at room temperature for 16 h, diluted with benzene (50 mL), filtered and the solvent removed under reduced pressure. The residue was chromatographed on alumina using benzene as eluent. The solvent was removed under reduced pressure to give the title compound (3.0 g, 82%) as a pale yellow oil.

Aufarbeitung

  1. filtrationfiltered
  2. customthe solvent removed under reduced pressure
  3. customThe residue was chromatographed on alumina
  4. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a0ff9380560945bba129be135c49328e
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703978B2

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