Trifluoroacetic anhydride → 6-ethyl-1H-indole

HRID 2215824Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2215824
FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(O[CH:17](OCC)[CH2:18][NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH3:27])[CH:21]=1)C>FC(F)(F)C(O)=O>[CH2:26]([C:22]1[CH:21]=[C:20]2[C:25]([CH:17]=[CH:18][NH:19]2)=[CH:24][CH:23]=1)[CH3:27]

Komponenten

4

Edukt 2

HCID 9845Trifluoroacetic anhydrideHCID 21949966(2,2-Diethoxyethyl)-(3-ethylphenyl)amine

Produkt 1

HCID 183302676-ethyl-1H-indoleAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel2×

Versuchsvorschrift

To a solution of trifluoroacetic anhydride (45 mL) in trifluoroacetic acid (45 mL) at 4° C. under N2 was added (2,2-diethoxyethyl)-(3-ethylphenyl)amine (11.47 g, 48.36 mmol). After stirring for 30 min, the cold mixture was diluted with trifluoroacetic acid (60 mL). The mixture was stirred at reflux for 2.5 d, concentrated and extracted with methylene chloride (3×100 mL). The combined organic layers were washed with saturated NaHCO3 (3×60 mL), saturated NaCl (60 mL), dried (MgSO4) and concentrated. Flash chromatography (SiO2, 25% EtOAc/hexanes) gave the title compound (1.6 g, 23%) as a brown crystalline solid. 1H NMR (CDCl3) δ 8.03 (bs, 1H), 7.57 (m, 1H), 7.18 (s, 1H), 7.12 (m, 1H), 6.68 (m, 1H), 6.46 (m, 1H), 2.73 (m, 2H), 1.26 (m, 3H)

Aufarbeitung

  1. stirringThe mixture was stirred
  2. temperatureat reflux for 2.5 d
  3. concentrationconcentrated
  4. extractionextracted with methylene chloride (3×100 mL)
  5. washThe combined organic layers were washed with saturated NaHCO3 (3×60 mL), saturated NaCl (60 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-140bd818cda14873b56a6f784d8589ae
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07109229B2

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