Oxalic Acid → 3-Methylindole-1-acetaldehyde

HRID 596951

Reaktionsgleichung

Reaktionsgleichung von HRID 596951
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH2:12][OH:13])[CH:3]=1.FC(F)(F)C(O)=O.N1C=CC=CC=1.C(O)(=O)C(O)=O>CS(C)=O.C1C=CC=CC=1.CCOCC.CO.O>[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:11][CH:12]=[O:13])[CH:3]=1

Komponenten

9

Edukt 4

HCID 971Oxalic AcidHCID 1049PyridineHCID 6422Trifluoroacetic acidHCID 122267423-Methylindole-1-ethanol

Produkt 1

HCID 545647933-Methylindole-1-acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 18518713Benzene dimethylsulfoxideLösungsmittel

Versuchsvorschrift

N,N-dicyclohexylcarbodiimide (9.0 g) is added to a cooled, stirred solution of 3-methylindole-1-ethanol (3.0 g) in 30 ml of dimethyl sulfoxide-benzene (2:1) containing trifluoroacetic acid (0.6 ml) and pyridine (1.12 ml). The reaction is stirred at room temperature under nitrogen for 5 hours. The reaction mixture is now diluted with 300 ml of ether, followed by the dropwise addition of a solution of oxalic acid (3.78 g) in 11 ml of methanol. After 30 minutes, water (300 ml) is added and the insoluble material is collected. The organic phase is washed with water (2X), 5% aqueous sodium bicarbonate (2 X) and water (2X). After drying (MgSO4) the organic phase is evaporated to yield 3-methylindole-1-acetaldehyde. The latter compound is then converted to its corresponding gem-dithiol with hydrogen sulfide and reduced with lithium aluminium hydride according to the method of T. L. Cairns et al., J. Amer. Chem. Soc., 74, 3982 (1952), to yield the title compound, γ maxCHCl3 2570 cm-1.

Aufarbeitung

  1. waitAfter 30 minutes
  2. customthe insoluble material is collected
  3. washThe organic phase is washed with water (2X), 5% aqueous sodium bicarbonate (2 X) and water (2X)
  4. dry with materialAfter drying (MgSO4) the organic phase
  5. customis evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2cd23ad76789480585933acb8e317ff6
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04012511

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