Water → 1H-Indole, 4-methoxy-1-(phenylmethyl)-

HRID 567376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 567376
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[CH:8][NH:9]2.[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN(C=O)C>[CH2:14]([N:9]1[C:10]2[C:6](=[C:5]([O:4][CH3:3])[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 1383634-Methoxy-1H-indole

Produkt 1

HCID 107285831H-Indole, 4-methoxy-1-(phenylmethyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (7.7 g, 191.7 mmol) was added portionwise to a 0° C. solution of 4-methoxyindole (21.7 g, 147 mmol) in 750 mL of anhydrous DMF. After 15 min, the slurry was treated with benzyl bromide (17.5 mL, 147 mmol). The reaction mixture was allowed to warm to ambient temperature and stir overnight. The reaction mixture was poured into 1 L of H2O. The layers were separated, and the aqueous phase was extracted with EtOAc (2×200 mL). The combined organic layers were washed with H2O (4×500 mL), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2; hexanes) to give 32.9 g (138.6 mmol; 94%) of the title compound as a white solid. Electrospray MS 238 (M+1);

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×200 mL)
  3. washThe combined organic layers were washed with H2O (4×500 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (SiO2; hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-36b4eb5564264aae8defa89d43121e36
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06177440B1

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