Hexane → Methyl 4-[2-(1,1-dimethyl-3-oxo-indan-5-yl)vinyl]benzoate

HRID 53285

Reaktionsgleichung

Reaktionsgleichung von HRID 53285
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:13])([CH3:12])[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=[CH2:15].C(=O)(O)[O-].[Na+].CCCCCC>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.C(Cl)Cl>[CH3:12][C:6]1([CH3:13])[C:5]2[C:9](=[CH:10][C:2]([CH:15]=[CH:14][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)=[CH:3][CH:4]=2)[C:8](=[O:11])[CH2:7]1

Komponenten

11

Edukt 4

HCID 8058HexaneHCID 516892Sodium BicarbonateHCID 583124Methyl 4-ethenylbenzoateHCID 107763656-bromo-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

Produkt 1

HCID 54336622Methyl 4-[2-(1,1-dimethyl-3-oxo-indan-5-yl)vinyl]benzoateAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 6

HCID 167845palladium(II) acetateKatalysatorHCID 16212273Tetrabutylammonium chloride hydrateKatalysatorHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Bromo-3,3-dimethyl-indan-1-one (1.20 g, 5.02 mmol), methyl 4-vinylbenzoate (1.63 g, 10.0 mmol), palladium acetate (56 mg, 0.25 mmol), tetrabutylammonium chloride hydrate (1.53 g, 5.52 mmol ), and sodium bicarbonate (1.05 g, 12.6 mmol) were stirred in 10 mL of anhydrous N,N-dimethylformamide at 80°-100° C. for 8 hours. The mixture was diluted with water (100 mL), extracted with methylene chloride (50 mL×3). The combined extracts were dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (CH2Cl2 :hexane=1:1 to 1:0, then CH2Cl2 :EtOAc=10:1) to give 1.12 g (70% yield) of the title compound as a yellow solid; 1H-NMR (CDCl3) δ1.45 (s, 6H), 2.64 (s, 2H), 5.30 (s, 3H), 7.18 (d, J=16.5 Hz, 1H), 7.26 (d, J=16.5 Hz, 1H), 7.52 (d, J=8.1 Hz, 1H), 7.58 (d, J=8.5 Hz, 2H), 7.78 (d, J=1.7, 8.1 Hz, 1H), 7.86 (d, J=1.7 Hz, 1H), 8.05 (d, J=8.5 Hz, 2H); MS m/e 321 (MH+).

Aufarbeitung

  1. extractionextracted with methylene chloride (50 mL×3)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. customevaporated
  4. customThe residue was purified by flash chromatography (CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-e894fad907b74d91b47cdd45f501a1db
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618839

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