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Triphenylphosphine → 3-[(4-Dibutylaminophenyl)ethynyl]-2-naphthol

HRID 2369633
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Reaktionsgleichung

Reaktionsgleichung von HRID 2369633
C([Si](C(C)C)(C(C)C)[O:5][C:6]1[CH:7]=[C:8](Br)[C:9]2[C:14]([CH:15]=1)=[CH:13][CH:12]=[CH:11][CH:10]=2)(C)C.[C:23]([C:25]1[CH:39]=[CH:38][C:28]([N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH3:33])=[CH:27][CH:26]=1)#[CH:24].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CCN(CC)CC.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.O>[CH2:30]([N:29]([CH2:34][CH2:35][CH2:36][CH3:37])[C:28]1[CH:27]=[CH:26][C:25]([C:23]#[C:24][C:7]2[C:6]([OH:5])=[CH:15][C:14]3[C:9]([CH:8]=2)=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:39][CH:38]=1)[CH2:31][CH2:32][CH3:33]
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Komponenten

9

Edukt 4

HCID 11776TriphenylphosphineHCID 2724141Tetrabutylammonium FluorideHCID 12249159N,N-dibutyl-4-ethynylanilineHCID 671624644-Bromo-2-triisopropylsiloxynaphthalene

Produkt 1

HCID 671627463-[(4-Dibutylaminophenyl)ethynyl]-2-naphtholAusbeute 44,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 962WaterLösungsmittel2×
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

A solution of 3-triisopropylsilyoxy-1-bromonaphthalene (3.17 g, 8.4 mmol), 4-ethynyl-N,N-dibutylaniline (2.87 g, 12.5 mmol), Pd(PPh3)2Cl2 (176 mg, 3 mol %), PPh3 (329 mg, 15 mol %) and CuI (120 mg, 7.5 mol %) in Et3N (20 mL) under N2 was heated at reflux for 3 h. The resulting mixture was cooled, poured into water (200 mL), extracted with DCM (3×50 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was chromatographed on silica using DCM (20% in hexanes) as eluent. The solvent was removed under reduced pressure and the residue dissolved in Et2O (30 mL). Tetrabutylammonium fluoride (3.8 mL, 1 M, 3.8 mmol) was added and stirring continued for 10 min. The solution was poured into water (100 mL), extracted with Et2O (3×40 mL), dried (MgSO4) and the solvent removed under reduced pressure. The residue was filtered through a short plug of silica using DCM (15% in hexanes to 0% in EtOAc gradient) as eluent. The solvent was removed under reduced pressure to give the title compound (1.40 g, 21%) as a brown oil.

Aufarbeitung

  1. temperatureat reflux for 3 h
  2. temperatureThe resulting mixture was cooled
  3. extractionextracted with DCM (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure
  6. customThe residue was chromatographed on silica
  7. customThe solvent was removed under reduced pressure
  8. dissolutionthe residue dissolved in Et2O (30 mL)
  9. extractionextracted with Et2O (3×40 mL)
  10. dry with materialdried (MgSO4)
  11. customthe solvent removed under reduced pressure
  12. filtrationThe residue was filtered through a short plug of silica
  13. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b5eb59f967454a239a0a5c7bf1eb10e6
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08703978B2

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