Trifluoroacetic acid → HCID 46914013, Verbindung

HRID 597846Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597846
FC(F)(F)[C:3](O)=[O:4].[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][CH:15]=1)[CH3:9].COC(OC)OC.[OH-].[Na+]>O.C(OCC)(=O)C>[CH2:8]([O:10][C:11](=[O:24])[CH2:12][CH2:13][C:14]1[C:22]2[C:21](=[O:23])[CH2:20][CH2:19][CH2:18][C:17]=2[NH:16][C:15]=1[CH:3]=[O:4])[CH3:9]

Komponenten

7

Edukt 4

HCID 6422Trifluoroacetic acidHCID 9005Trimethyl orthoformateHCID 14798Sodium HydroxideHCID 46914009HCID 46914009, Verbindung

Produkt 1

HCID 46914013HCID 46914013, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a trifluoroacetic acid solution (47 mL) containing 3-(3-ethoxy-3-oxopropyl)-4-oxo-4,5,6,7-tetrahydro-1H-indole (4, 10.0 g, 42.5 mmol) was added with trimethylorthoformate (13.6 g, 128 mmol) at 0° C. The reaction was stirred at 0° C. for 30 min, warmed up to room temperature and stirred for 2.0 h. The solution was added with ethyl acetate (250 mL), water (200 mL) and NaOH (18 g). The organic layer was collected and washed with saturated aqueous NaHCO3 (200 mL), dried over MgSO4 (s), and concentrated under reduced pressure. The oily residue was purified by gravity column chromatography (50% EtOAc in hexanes) to give 3-(3-ethoxy-3-oxopropyl)-2-formyl-4-oxo-4,5,6,7-tetrahydro-1H-indole (5, 2.1 g, 8.0 mmol) as yellow solids in 19% yield.

Aufarbeitung

  1. temperaturewarmed up to room temperature
  2. stirringstirred for 2.0 h
  3. customThe organic layer was collected
  4. washwashed with saturated aqueous NaHCO3 (200 mL)
  5. dry with materialdried over MgSO4 (s)
  6. concentrationconcentrated under reduced pressure
  7. customThe oily residue was purified by gravity column chromatography (50% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9e917815dc6a42dea3435fc387666331
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897602B2

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