Diethyl Ether → HCID 68822475, Verbindung

HRID 751196

Reaktionsgleichung

Reaktionsgleichung von HRID 751196
[C:1]([Si:5]([CH3:17])([CH3:16])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]=[CH:10]2)([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)C>CN(C=O)C>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][N:12]1[C:13]2[C:9](=[CH:8][C:7]([O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:17])[CH3:16])=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)[CH3:24]

Komponenten

6

Edukt 4

HCID 3283Diethyl EtherHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 222508175-(tert-Butyldimethylsilyloxy)-1H-indole

Produkt 1

HCID 68822475HCID 68822475, VerbindungAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A suspension of 5-(tert-butyl-dimethyl-silanyloxy)-1H-indole (9.2 g, 37.2 mmol), ethyl bromoacetate (4.79 ml, 40.9 mmol) and cesium carbonate (36.4 g, 111.5 mmol) in DMF (140 ml) was stirred for 3 h at RT. Diethyl ether was added and the mixture was washed with 1N HCl and water, and dried over sodium sulfate. The ether phase was concentrated under reduced pressure to give 12.9 g (quant.) of [5-(tert-butyl-dimethyl-silanyloxy)-indol-1-yl]-acetic acid ethyl ester which was used in the next step without further purification.

Aufarbeitung

  1. washthe mixture was washed with 1N HCl and water
  2. dry with materialdried over sodium sulfate
  3. concentrationThe ether phase was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f114a15fa2904497aae4de17a35e5f31
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405236B2

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