4-[(phenylmethyl)oxy]-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole → 1-(4-hydroxyphenyl)-1H-indol-4-ol

HRID 2421263Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421263
C1(C[O:8][C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH:11]=[CH:12][N:13]3[C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC=CC=3)=[CH:20][CH:19]=2)C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:24][C:21]1[CH:22]=[CH:23][C:18]([N:13]2[C:14]3[CH:15]=[CH:16][CH:17]=[C:9]([OH:8])[C:10]=3[CH:11]=[CH:12]2)=[CH:19][CH:20]=1

Komponenten

4

Edukt 1

HCID 596279224-[(phenylmethyl)oxy]-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole

Produkt 1

HCID 441932861-(4-hydroxyphenyl)-1H-indol-4-olAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-[(phenylmethyl)oxy]-1-{4-[(phenylmethyl)oxy]phenyl}-1H-indole (D24) (143 mg, 0.352 mmoL) was dissolved in ethyl acetate (10 mL) and was hydrogenated at room temperature and atmospheric pressure in the presence of 10% palladium on charcoal (50% wet) (70 mg). After 28 hours the mixture was filtered and concentrated in vacuo. The crude product was purified by flash chromatography (Biotage SP4) eluting with a gradient of 0 to 100% ethyl acetate in hexane to give the title compound (E14), (55 mg).

Aufarbeitung

  1. customwas hydrogenated at room temperature
  2. filtrationAfter 28 hours the mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash chromatography (Biotage SP4)
  5. washeluting with a gradient of 0 to 100% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-3156e487db4e4785906a5906bc47ab6f
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07956083B2

Notizen zur Reaktion

Wird geladen…