Ethyl Acetate → 5-Methoxy-1H-indole-2-carbaldehyde

HRID 1883203

Reaktionsgleichung

Reaktionsgleichung von HRID 1883203
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12](O)=[O:13])=[CH:6]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C>CCOCC.Cl.C1COCC1.O=[Mn]=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([CH:12]=[O:13])=[CH:6]2

Komponenten

8

Edukt 3

HCID 8857Ethyl AcetateHCID 204015-Methoxyindole-2-carboxylic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 8264565-Methoxy-1H-indole-2-carbaldehydeAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 14801Manganese dioxideKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under nitrogen atmosphere, to a solution of 5-methoxyindole-2-carboxylic acid (1.00 g) in Et2O (40 mL) was added LiAlH4 (280 mg) at 0° C., and the mixture was stirred under reflux for 3 hours. The mixture was treated with ethyl acetate, diluted with an aqueous hydrochloric acid solution, and extracted with ethyl acetate. The mixture was concentrated to give a crude alcohol compound (840 mg, 91%), which was dissolved in THF (10 mL), and stirred with MnO2 (4.20 g) at room temperature for 5 hours. The mixture was filtered on celite, and the filtrate was concentrated, and the residue was purified by silica gel column chromatography to give 5-methoxyindole-2-carbaldehyde (300 mg, 36%).

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. extractionextracted with ethyl acetate
  3. concentrationThe mixture was concentrated
  4. customto give a crude alcohol compound (840 mg, 91%), which
  5. filtrationThe mixture was filtered on celite
  6. concentrationthe filtrate was concentrated
  7. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3f1376d864da42359218ce88038a9077
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06759429B2

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