Acetic Acid → (5-Hydroxy-indol-1-yl)-acetic acid ethyl ester

HRID 490676

Reaktionsgleichung

Reaktionsgleichung von HRID 490676
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15]CC3C=CC=CC=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2].C(O)(=O)C.[H][H]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH3:2]

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 59897880HCID 59897880, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 57675474(5-Hydroxy-indol-1-yl)-acetic acid ethyl esterAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel2×

Versuchsvorschrift

(5-Benzyloxy-indol-1-yl)-acetic acid ethyl ester (3.49 g, 11.31 mmol) is dissolved in EtOH (50 mL) and glacial acetic acid is added (2.0 mL). Palladium on carbon (20% by wt., 0.700 g) is then added to the homogenous solution, and a hydrogen filled balloon is connected to the round bottom flask. A vacuum is created within the flask until the ethanol began to bubble, and the hydrogen allowed to enter the flask; this procedure is repeated three times, then the reaction is left to stir at room temperature overnight. Upon completion, the reaction is diluted with DCM (200 mL), and water (100 mL) is added. The mixture is filtered through a celite plug and the two phases are separated. The organic layer is washed with brine (2×75 mL), then dried over anhydrous magnesium sulfate, and concentrated to yield the title compound (2.42 g) in 98% yield. The residual acetic acid is removed by flash column chromatography.

Aufarbeitung

  1. customto bubble
  2. waitthe reaction is left
  3. additionUpon completion, the reaction is diluted with DCM (200 mL), and water (100 mL)
  4. additionis added
  5. filtrationThe mixture is filtered through a celite plug
  6. customthe two phases are separated
  7. washThe organic layer is washed with brine (2×75 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4376cf47968e40aab703875e433b771e
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528160B2

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