Dimethylformamide → Methyl (2,3-dihydro-1H-indol-1-yl)acetate

HRID 55474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 55474
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[N:7]1([CH2:2][C:3]([O:5][CH3:6])=[O:4])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8]1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10328IndolineHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate

Produkt 1

HCID 22199910Methyl (2,3-dihydro-1H-indol-1-yl)acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

0.40 ml of methyl bromoacetate was added dropwise to a mixture of 0.25 g of indoline, 2 ml of dimethylformamide and 0.87 g of anhydrous potassium carbonate, and the resulting mixture was stirred at room temperature for 1 hour. At the end of this time, the reaction mixture was poured into water, after which it was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 5:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.30 g of the title compound having Rf=0.63 (on silica gel thin layer chromatography using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent).

Aufarbeitung

  1. extractionafter which it was extracted with ethyl acetate
  2. washThe extract was washed with an aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of hexane and ethyl acetate as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-e52a6417b2a644ad95dfade076722b95
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05624935

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