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1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole → 1-(3-Hydroxybenzyl)-5-methoxy-2-phenylindole

HRID 1191651
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1191651
C([O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)C1C=CC=CC=1>FC(F)(F)C(O)=O.O.CSC>[OH:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][CH:32]=1)[CH2:12][N:13]1[C:21]2[C:16](=[CH:17][C:18]([O:22][CH3:23])=[CH:19][CH:20]=2)[CH:15]=[C:14]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

3

Edukt 1

HCID 696710521-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole

Produkt 1

HCID 696709171-(3-Hydroxybenzyl)-5-methoxy-2-phenylindoleAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 86597598Trifluoroacetic acid water dimethylsulfideLösungsmittel

Versuchsvorschrift

1-(3-Benzyloxybenzyl)-5-methoxy-2-phenylindole (200 mg) was dissolved in trifluoroacetic acid-water-dimethyl sulfide (95/5/10, 4.8 mL), and the solution was stirred at room temperature for 68 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (110 mg).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washThe solution was washed successively with a saturated aqueous sodium hydrogen carbonate solution and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-017956df7c7b4e1596a409f3717b2702
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08680120B2

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