Diazomethane → Methyl indole-3-carboxylate

HRID 128993

Reaktionsgleichung

Reaktionsgleichung von HRID 128993
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[CH:2]1.[N+](=[CH2:15])=[N-]>CCOCC.C(OCC)(=O)C.CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([O:12][CH3:15])=[O:11])=[CH:2]1

Komponenten

6

Edukt 2

HCID 9550DiazomethaneHCID 69867Indole-3-Carboxylic Acid

Produkt 1

HCID 589098Methyl indole-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Indole-3-carboxylic acid (757 mg, 4.7 mmol, 1.0 eq.) was partially dissolved in a mixture of ether, ethyl acetate and methanol. While stirring, a solution of diazomethane in ether was added until a yellow color persisted. The solvent was removed in vacuo and the remaining white solid was passed through a silica gel column, eluting with dichloromethane to give the title A compound (819 mg), m.p. 147°-149° C.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. washeluting with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-1c8c10f69faf4487bee50351a9363e9b
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05466704

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