Potassium Carbonate → 4,5-Dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile

HRID 2078795Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2078795
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1)[C:5]#[N:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[S:15]1[C:14]2[C:2]3[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=3[O:10][CH2:11][CH2:12][C:13]=2[CH:17]=[CH:16]1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 568341533-Bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile

Produkt 1

HCID 568341544,5-Dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 3-bromo-4-(2-thiophen-3-yl-ethoxy)-benzonitrile (4.50 g) in DMF (20 mL) was added palladium acetate (327 mg), triphenylphosphine (766 mg) and potassium carbonate (4.03 g) and the reaction heated at 90° C. for 16 h. After cooling to room temperature the mixture was diluted with ethyl acetate (60 ml) and filtered. The filtrate was washed with brine (80 mL), dried (MgSO4), reduced in vacuo and purified on silica to give 4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-9-carbonitrile.

Aufarbeitung

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationfiltered
  3. washThe filtrate was washed with brine (80 mL)
  4. dry with materialdried (MgSO4)
  5. custompurified on silica

Quellen und Nachweise

ORD-Eintrag
ord-89d49eef1c2d42c79c343a830fc03e31
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07928248B2

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