Tetrahydrofuran → Methyl 7-hydroxy-1-methyl-2-indolecarboxylate

HRID 1067774Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1067774
O1CCCC1.C([O:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19]2)C1C=CC=CC=1>[Pd].CO>[OH:13][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:22]=1[N:21]([CH3:23])[C:20]([C:24]([O:26][CH3:27])=[O:25])=[CH:19]2

Komponenten

5

Edukt 2

HCID 8028TetrahydrofuranHCID 15550275Methyl 7-benzyloxy-1-methyl-2-indolecarboxylate

Produkt 1

HCID 21194122Methyl 7-hydroxy-1-methyl-2-indolecarboxylateAusbeute 101,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

In a solvent mixture of 50 ml of tetrahydrofuran and 50 ml of methanol was dissolved 2.31 g (7.82 mmol) of methyl 7-benzyloxy-1-methyl-2-indolecarboxylate. After 0.5 g of 10% palladium/carbon was added to the solution, catalytic hydrogenation was performed at ambient temperature under normal pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to give 1.63 g (>99%) of methyl 7-hydroxy-1-methyl-2-indolecarboxylate.

Aufarbeitung

  1. customwas performed at ambient temperature under normal pressure
  2. customAfter completion of the reaction
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bdfadd9243364201ace977254ddad157
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06248772B1

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