Ethanol → Methyl indole-6-carboxylate

HRID 1242125

Reaktionsgleichung

Reaktionsgleichung von HRID 1242125
O1CCCC1.C(O)C.CN(C)/[CH:11]=[CH:12]/[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[N+:23]([O-])=O.S(S([O-])=O)([O-])=O.[Na+].[Na+]>O>[CH3:20][O:19][C:17]([C:16]1[CH:15]=[C:14]2[C:13]([CH:12]=[CH:11][NH:23]2)=[CH:22][CH:21]=1)=[O:18]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 24489Sodium DithioniteHCID 894337(E)-Methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate

Produkt 1

HCID 639844Methyl indole-6-carboxylateAusbeute 39,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a mixed solvent of tetrahydrofuran (30 ml), ethanol (30 ml) and water (100 ml), added are methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (10.0 g) and sodium hydrosulfite (104.5 g), and stirred at 70° C. for 1 hours. After this is cooled to room temperature, a saturated saline solution is added thereto. Then, this is extracted with chloroform. The organic layer is dried, and the solvent is evaporated away. The resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1) to obtain 6-methoxycarbonylindole (2.79 g).

Aufarbeitung

  1. temperatureAfter this is cooled to room temperature
  2. additiona saturated saline solution is added
  3. extractionThen, this is extracted with chloroform
  4. customThe organic layer is dried
  5. customthe solvent is evaporated away
  6. customThe resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1)

Quellen und Nachweise

ORD-Eintrag
ord-c315ac36537f4e9db6abb6977f887501
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115647B2

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