Diazomethane → methyl 1H-indole-4-carboxylate

HRID 247854

Reaktionsgleichung

Reaktionsgleichung von HRID 247854
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[CH:2]1.[N+](=[CH2:15])=[N-].S([O-])([O-])(=O)=O.[Mg+2]>CO.C(OCC)C>[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:15])=[O:11])[C:4]=2[CH:3]=[CH:2]1

Komponenten

6

Edukt 3

HCID 9550DiazomethaneHCID 24083Sulfuric acid magnesium salt (1:1)HCID 595229Indole-4-carboxylic acid

Produkt 1

HCID 2733668methyl 1H-indole-4-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of indole-4-carboxylic acid (506 mg, 3.14 mmol) dissolved in a mixture of methanol (5 mL) and diethyl ether (10 mL) was added ethereal diazomethane until disappearance of the starting acid was indicated by TLC. Magnesium sulfate was then added and the solution filtered and concentrated in vacuo. Flash chromatography on Merck silica gel (10 g) eluted with 2:1, chloroform:hexanes, followed by 10:1, chloroform: ether afforded the title compound (540 mg, 98%).

Aufarbeitung

  1. filtrationthe solution filtered
  2. concentrationconcentrated in vacuo
  3. washFlash chromatography on Merck silica gel (10 g) eluted with 2:1, chloroform

Quellen und Nachweise

ORD-Eintrag
ord-f3eca2e7cd8b4af0b2f619fef1d40c9d
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05208235

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