Triphenylphosphine → HCID 22650026, Verbindung

HRID 393301Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 393301
Br[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:37][Si:38]([C:41]#[CH:42])([CH3:40])[CH3:39]>C(NC(C)C)(C)C.CCCCCC.O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:37][Si:38]([CH3:40])([CH3:39])[C:41]#[C:42][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6](=[CH2:13])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[CH:3]=1

Komponenten

7

Edukt 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 10107850HCID 10107850, Verbindung

Produkt 1

HCID 22650026HCID 22650026, VerbindungAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 165397Cupric acetate monohydrateKatalysatorHCID 7912DiisopropylamineLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of 4 (5.66 g, 20 mmol), dichlorobis(triphenylphosphine) palladium(II) (0.7 g, 1 mmol), copper(II) acetate hydrate (0.18 g, 1 mmol) and triphenyl-phosphine (0.52 g, 2 mmol) in 40 mL of diisopropyl amine was added trimethylsilyl acetylene (2.16 g, 22 mmol) and heated to reflux. On refluxing for an hour the mixture turns dark and solidifies. The reaction mixture was diluted with 50 mL of hexane and filtered. The filtrate was concentrated under reduced pressure and the residue was chromatographed over silica gel with hexane/methylene chloride (9:1 by volume) as eluant to yield 2.88 g (50 percent) of trimethyl[2-(5-methylene-5H-dibenzo[a,d]cyclohepten-10-yl)ethynyl)silane, 5, as a yellow oil.

Aufarbeitung

  1. temperatureheated to reflux
  2. temperatureOn refluxing for an hour the mixture
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was chromatographed over silica gel with hexane/methylene chloride (9:1 by volume) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-1938dc19cfc54d7684f8650cbf298e53
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06806327B2

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