Triethylamine → 2-[4-(2-Ethoxycarbonylvinyl)naphthyl]dioxolane

HRID 1166742Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166742
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)=[CH:9][CH:8]=1)(=O)=O.[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=[CH2:26].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:29]([O:28][C:24]([CH:25]=[CH:26][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)=[CH:9][CH:8]=1)=[O:27])[CH3:30]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 540831252-(4-Trifluoromethylsulfonyloxy naphthyl)dioxolane

Produkt 1

HCID 536829332-[4-(2-Ethoxycarbonylvinyl)naphthyl]dioxolaneAusbeute 53,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

Nitrogen was passed through a solution of 2-(4-trifluoromethylsulfonyloxynaphthyl) dioxolane (2.46 g, 7.06 mmol), ethyl acrylate (2.3 mL, 2.1 g, 21.2 mmol), triethylamine (4.3 g, 42.3 mmol) in DMF (6 mL) for 15 min, and bis(triphenylphosphine)palladium dichloride was added. The well stirred solution was heated at 90° C. for 8 hr, and concentrated. The residue was dissolved in ethyl acetate (50 mL), washed with brine (2×50 mL), dried (Na2SO4), and concentrated. Purification by flash chromatography using hexane/ethyl acetate 9:1 as eluent provided a yellow solid (1.13 g, 53%).

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with brine (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ae5062cc5897487ab8c327f54d0e14e1
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613942B1

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