Hydrochloric Acid → HCID 54121458, Verbindung

HRID 278443

Reaktionsgleichung

Reaktionsgleichung von HRID 278443
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([O:15][CH3:16])=[CH:10][CH:9]=2)=[O:5])C.[Mg].Cl>CO>[CH3:1][O:3][C:4]([CH:6]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:15][CH3:16])[CH:12]=2)[NH:7]1)=[O:5]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 20926Ethyl 5-methoxyindole-2-carboxylateHCID 5462224Magnesium

Produkt 1

HCID 54121458HCID 54121458, VerbindungAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To 5-methoxy-1H-indole-2-carboxylic acid ethyl ester (5 g, 22.8 mmol) in MeOH (150 ml) was added magnesium turnings (2.2 g, 91.6 mmol, 4eq.) and the mixture vigorously mechanically stirred (10-30° C.) for 2 hr. 4N HCl was added (to pH1-2), then 25% NH4OH (to pH 7), and the mixture extracted with EtOAc (4×100 ml). The combined extracts were then washed with satd. NaCl solution (50 ml), dried (Na2SO4) filtered and evaporated. The crude green oil was chromatographed over SiO2 (Merck 230-400 mesh) eluting with EtOAc-nHexane (1:3) to afford the title compound (3.21g, 15.5 mmol, 68%) as a yellow solid Mp. 59-61° C., MS: m/e=207.1 (M+).

Aufarbeitung

  1. extraction25% NH4OH (to pH 7), and the mixture extracted with EtOAc (4×100 ml)
  2. washThe combined extracts were then washed with satd
  3. dry with materialNaCl solution (50 ml), dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude green oil was chromatographed over SiO2 (Merck 230-400 mesh)
  7. washeluting with EtOAc-nHexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-86fd5dc6478247c9beb8be490dc96900
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06359138B1

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