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Sodium hydride → Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-1H-indol-5-yl ester

HRID 1887637
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1887637
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11](=[O:17])[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:20][C:21]([Si:24](Cl)([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C1COCC1>[C:21]([Si:24]([CH3:26])([CH3:25])[N:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C:11](=[O:17])[N:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)([CH3:23])([CH3:22])[CH3:20]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 28928tert-Butyldimethylsilyl chlorideHCID 10331501Diethyl-carbamic acid 1H-indol-5-yl ester

Produkt 1

HCID 9975323Diethyl-carbamic acid 1-(tert-butyl-dimethyl-silanyl)-1H-indol-5-yl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Diethyl-carbamic acid 1H-indol-5-yl ester (5.72 g, 24.6 mmol) is dissolved in THF (200 mL) and cooled to 0° C. The flask is purged with nitrogen and then 60% NaH (1.1 g, 27.5 mmol) is added and the mixture stirred in aen ice bath for 30 minutes. At that point TBDMSCl (0.210 g, 1.39 mmol) is added and the reaction is allowed to stir overnight (14 hours). The reaction is quenched with a saturated solution of ammonium chloride and the mixture is diluted with ethyl acetate and water. The organic layer is removed, dried (sodium sulfate) and concentrated to obtain the title compound as an oil that is used without further purification. MS (ESI) m/z 347.21 (M+1).

Aufarbeitung

  1. customThe flask is purged with nitrogen
  2. stirringto stir overnight (14 hours)
  3. customThe reaction is quenched with a saturated solution of ammonium chloride
  4. additionthe mixture is diluted with ethyl acetate and water
  5. customThe organic layer is removed
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2178d3aa45da4e099d5baf0fa5e397fb
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501756B2

Notizen zur Reaktion

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