Diazomethane diethylether → Methyl 4-chloro-3,7-dimethylindole-2-carboxylate

HRID 361612

Reaktionsgleichung

Reaktionsgleichung von HRID 361612
[N+](=[CH2:3])=[N-].CCOCC.[Cl:9][C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:11]=1[C:12]([CH3:23])=[C:13]([C:20]([OH:22])=[O:21])[NH:14]2>CCOCC>[Cl:9][C:10]1[CH:18]=[CH:17][C:16]([CH3:19])=[C:15]2[C:11]=1[C:12]([CH3:23])=[C:13]([C:20]([O:22][CH3:3])=[O:21])[NH:14]2

Komponenten

4

Edukt 2

HCID 21186548Diazomethane diethyletherHCID 541380234-Chloro-3,7-dimethylindole-2-carboxylic acid

Produkt 1

HCID 54167277Methyl 4-chloro-3,7-dimethylindole-2-carboxylateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

An excess diazomethane ether solution was added to an ether solution of 0.50 g (2.24 mmol) of 4-chloro-3,7-dimethylindole-2-carboxylic acid under ice-cooling. The reaction mixture was allowed to stand for 30 minutes and then washed with 1N HCl aqueous solution and aqueous saturated sodium chloride solution. The ether layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to provide white crystals. The crude crystals were purified by silica gel column chromatography to provide 0.41 g of white crystals. Yield: 77%

Aufarbeitung

  1. temperaturecooling
  2. washwashed with 1N HCl aqueous solution and aqueous saturated sodium chloride solution
  3. dry with materialThe ether layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto provide white crystals
  6. customThe crude crystals were purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5c78a918d90a45fd82ec6dcd9951ca10
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866594

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