Triphenylphosphine → HCID 69991334, Verbindung

HRID 2299188Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299188
Br[C:2]1[CH:21]=[CH:20][C:5]2[O:6][C:7]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[C:12]([O:18][CH3:19])[C:8]=3[C:9](=[O:11])[CH2:10][C:4]=2[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(C(C)C)CC)(C)C.[C:50]([Si:52]([CH3:55])([CH3:54])[CH3:53])#[CH:51]>CN1CCCC1=O.C(OCC)(=O)C.[Cu](I)I>[CH3:17][O:16][C:14]1[CH:13]=[C:12]([O:18][CH3:19])[C:8]2[C:9](=[O:11])[CH2:10][C:4]3[C:3]([C:51]#[C:50][Si:52]([CH3:55])([CH3:54])[CH3:53])=[CH:2][CH:21]=[CH:20][C:5]=3[O:6][C:7]=2[CH:15]=1

Komponenten

8

Edukt 4

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 23431845HCID 23431845, Verbindung

Produkt 1

HCID 69991334HCID 69991334, VerbindungAusbeute 80,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Bromo-7,9-dimethoxy-10,11-dihydrodibenzo[b,f]oxepin-10-one 500 mg (F. W. 349.18, 1.43 mmol) prepared in the first stage of Production Example 79, triphenylphosphine 75 mg (F. W. 262.29, 0.062 mmol), trisbenzylidene acetone dipalladium chloroform complex 74 mg (F. W. 1035.08, 0.015 mmol), diisopropylethylamine 575 μl (F. W. 98.22, d=0.742, 2.86 mmol), ethynyl trimethylsilane 350 μl (F. W. 98.22, d=0.742, 2.86 mmol) and copper iodide 27.5 mg (F. W. 190.44, 0.143 mmol) were dissolved in N-methyl-2-pyrrolidone (5 ml) and, after substituting with argon atmosphere, they were stirred with heating at 80° C. for one hour. The reaction mixture was diluted with ethyl acetate and washed with water and saturated sodium chloride solution. The organic layer was dried and concentrated and the resulting residue was purified by a silica gel column chromatography to give the title compound 420 mg (F. W. 367.419, 66%). The peaks of this compound in 1H-NMR (400 MHz, CDCl3) were as follows.

Aufarbeitung

  1. washwashed with water and saturated sodium chloride solution
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customthe resulting residue was purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-6b168829bccc495ea8f058e912065a65
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495592B1

Notizen zur Reaktion

Wird geladen…