Benzyl chloroformate → 1-Benzyloxycarbonyl-5-chloro-3-formylindol

HRID 564846

Reaktionsgleichung

Reaktionsgleichung von HRID 564846
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]=[O:12].[H-].[Na+].[C:15](Cl)([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>O1CCCC1>[CH2:18]([O:17][C:15]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[C:5]([CH:11]=[O:12])=[CH:6]1)=[O:16])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

5

Edukt 3

HCID 10387Benzyl chloroformateHCID 24758Sodium hydrideHCID 27953745-chloro-1H-indole-3-carbaldehyde

Produkt 1

HCID 184739871-Benzyloxycarbonyl-5-chloro-3-formylindol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-chloro-3-formylindole (5.00 g) in tetrahydrofuran (135 ml) was added sodium hydride (60% oil suspension, 3.53 g). The mixture was stirred for 20 minutes at room temperature. Carbobenzoxychloride (6.64 ml) was added to the mixture. After being stirred for 1 hour at room temperature, the whole was poured into ice water. The mixture was extracted with ethyl acetate. The extract was washed with brine and dried over magnesium sulfate. The solution was concentrated to give a residue, which was subjected to silica gel chromatography. Elution with hexane-ethyl acetate (5:1) provided 1-benzyloxycarbonyl-5-chloro-3-formylindol (5.74 g) as a crystal.

Aufarbeitung

  1. stirringAfter being stirred for 1 hour at room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationThe solution was concentrated
  6. customto give a residue, which
  7. washElution with hexane-ethyl acetate (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-634f65947fe743918acd6f1641032b35
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06169102A

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