Potassium Carbonate → 4-(2-Methyl-5-oxo-1-cyclopenten-1-yl)benzonitrile

HRID 656187

Reaktionsgleichung

Reaktionsgleichung von HRID 656187
Br[C:2]1[C:3](=[O:8])[CH2:4][CH2:5][C:6]=1[CH3:7].C([O-])([O-])=O.[K+].[K+].[C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)#[N:16].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1(C)C=CC=CC=1.CCO.[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:7][C:6]1[CH2:5][CH2:4][C:3](=[O:8])[C:2]=1[C:20]1[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[CH:18][CH:19]=1

Komponenten

9

Edukt 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 27343264-Cyanophenylboronic acidHCID 44370092-Bromo-3-methyl-2-cyclopenten-1-one

Produkt 1

HCID 219861594-(2-Methyl-5-oxo-1-cyclopenten-1-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 1542701,5-Diphenylpenta-1,4-dien-3-one;palladiumKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Bromo-3-methyl-cyclopent-2-enone (Intermediate TEN1) (commercially available from Aldrich) (2.04 g, 11.4 mmol) and K2CO3 (3.16 g in 11 mL H2O) in toluene (45 mL) was treated with a solution 4-cyanophenylboronic acid (commercially available from Aldrich) (2.2 g, 15 mmol) in EtOH (27 mL). Tetrakis(triphenylphosphine) palladium(0) Pd(PPh3)4 (0.4 g), bis(dibenzylideneacetone) palladium(0), Pd2(dba)3 (0.055 g, ˜5 mol %) and triphenylphosphine (0.4 g) were added and the mixture was purged with N2 for 15 m. The mixture was heated to 80° C. for 15 h. The mixture was diluted with water and EtOAc:hexane. After extracting with EtOAc:hexane, the combined organic layers were dried over MgSO4, filtered and evaporated to dryness. The crude oil was purified by column chromatography on silica gel with CH2Cl2 to give 4-(2-methyl-5-oxo-cyclopent-1-enyl)-benzonitrile (Intermediate TEN2) 1.74 g.

Aufarbeitung

  1. customthe mixture was purged with N2 for 15 m
  2. additionThe mixture was diluted with water and EtOAc
  3. extractionAfter extracting with EtOAc
  4. dry with materialhexane, the combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude oil was purified by column chromatography on silica gel with CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-bb988a6eaad74860aad1d0206028cbfb
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071635B2

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