Sodium hydride → 1H-Indole-5-carboxylic acid, 1-(2-methoxyethyl)-, methyl ester

HRID 2170849Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2170849
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:17][CH2:18][O:19][CH3:20]>O>[CH3:20][O:19][CH2:18][CH2:17][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 2737635methyl 1H-indole-5-carboxylate

Produkt 1

HCID 671694841H-Indole-5-carboxylic acid, 1-(2-methoxyethyl)-, methyl esterAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of methyl 1H-indole-5-carboxylate (200 mg, 1.14 mmol) and sodium hydride (60% in oil, 39 mg, 1.71 mmol) in N,N-dimethylformanide (3 mL) was added 1-bromo-2-methoxyethane (190 mg, 1.37 mmol) at room temperature. Then the mixture was stirred at 60° C. for 2 hours. The mixture was poured into water (20 mL) and extracted with ethyl acetate (20 mL). The organic layer was washed with water (20 mL) and dried over sodium sulfate. After removal of the solvent, the residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1) to give 132 mg (50%) of the title compound as colorless syrup.

Aufarbeitung

  1. extractionextracted with ethyl acetate (20 mL)
  2. washThe organic layer was washed with water (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe residue was purified by column chromatography on silica gel eluting with n-hexane/ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-6cb6d67f4d0b4e939f6ee6e390536e4f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051296B2

Notizen zur Reaktion

Wird geladen…