Tributylamine → HCID 66691768, Verbindung

HRID 330821

Reaktionsgleichung

Reaktionsgleichung von HRID 330821
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]2[CH:17]=[CH:16][C:15](I)=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)[CH3:2].[CH2:19]([O:21][CH:22]([O:25]CC)[CH:23]=[CH2:24])[CH3:20].C(N(CCCC)CCCC)CCC.CCOC(C)=O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:19]([O:21][C:22](=[O:25])[CH2:23][CH2:24][C:15]1[CH:16]=[CH:17][C:12]([C:11]#[C:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)=[CH:13][CH:14]=1)[CH3:20]

Komponenten

8

Edukt 4

HCID 7622TributylamineHCID 8857Ethyl AcetateHCID 624773,3-Diethoxy-1-propene2×HCID 66691575HCID 66691575, Verbindung

Produkt 1

HCID 66691768HCID 66691768, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 70681Tetrabutylammonium ChlorideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To 1.80 g (5.17 mmol) 1-ethoxy-4-((4-iodophenyl)ethynyl)benzene (XII.1) in 24 mL DMF are added 2.36 mL (15.5 mmol) 3,3-diethoxy-propene, 3.69 mL (15.5 mmol) tributylamine, 1.44 g (5.17 mmol) tetrabutylammoniumchloride and 0.04 g (0.16 mmol) palladium(II)acetate under argon. The mixture is stirred at 120° C. for 12 h. After that time, 1.18 mL (7.76 mmol) 3,3-diethoxy-propene are added and the mixture is stirred at 120° C. for 5 d. After cooling, EtOAc is added and the mixture is washed with 1N potassium hydrogensulfate solution and water. The organic layer is dried over sodium sulphate and the solvent is evaporated. The residue is purified by column chromatography (silica gel; PE:DCM 1:1) to yield the desired product.

Aufarbeitung

  1. stirringthe mixture is stirred at 120° C. for 5 d
  2. temperatureAfter cooling
  3. washthe mixture is washed with 1N potassium hydrogensulfate solution and water
  4. dry with materialThe organic layer is dried over sodium sulphate
  5. customthe solvent is evaporated
  6. customThe residue is purified by column chromatography (silica gel; PE:DCM 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-caeaae0a8b5941e9b57e00af235f045f
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877754B2

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