Indole → Ethyl 3-indolylglyoxylate

HRID 1360583Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1360583
N1C=CC=CC=1.[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.Cl[C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(OCC)C>[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([C:17](=[O:23])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:8]1

Komponenten

5

Edukt 3

HCID 798IndoleHCID 1049PyridineHCID 20884Ethoxalyl chloride

Produkt 1

HCID 101242Ethyl 3-indolylglyoxylateAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Pyridine (40 mL, 492 mmol) was added in a single portion to a chilled solution (0° C.) solution of indole (48 g, 410 mmol) in diethyl ether (820 mL). Ethyl chlorooxoacetate (50 mL, 451 mmol) was added dropwise. The resulting suspension was allowed to warm to ambient temperature over a period of 20 hours. The solid was isolated by filtration and washed with diethyl ether. The solid was combined with water (1 L), stirred for 1 hour, and then isolated by filtration to provide 75 g of ethyl (1H-indol-3-yl)(oxo)acetate.

Aufarbeitung

  1. customThe solid was isolated by filtration
  2. washwashed with diethyl ether
  3. customisolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-f1f856663b0a4aa8ae59deb6d8fab41c
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879849B2

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