Diazomethane → methyl 1H-indole-4-carboxylate

HRID 52160

Reaktionsgleichung

Reaktionsgleichung von HRID 52160
[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 starting acid was indicated by TLC. Anhydrous magnesium sulfate was then added and the solution filtered and concentrated in vacuo. Flash chromatography on 10 g of Merck silica gel eluted with 2:1, chloroform:hexanes, followed by 10:1, chloroform:diethyl ether afforded the title compound (540 mg, 98%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5d171451110d4124a3baf16313134425
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616591

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