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Ethyl Acetate → 3-(t-Butyldiphenylsilyloxy)-3-(4-pyridyl)propylamine

HRID 18400
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 18400
[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]([CH:25]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH2:26][C:27]#[N:28])[Si:8]([C:21]([CH3:24])([CH3:23])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)C.O>[Si:8]([O:7][CH:25]([C:29]1[CH:34]=[CH:33][N:32]=[CH:31][CH:30]=1)[CH2:26][CH2:27][NH2:28])([C:21]([CH3:23])([CH3:24])[CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 219742193-(t-Butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile

Produkt 1

HCID 121366443-(t-Butyldiphenylsilyloxy)-3-(4-pyridyl)propylamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962
Water
Lösungsmittel
2×
HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (299 mg, 7.87 mmol) was suspended in anhydrous diethyl ether (10 ml) under a nitrogen atmosphere, a solution of the obtained 3-(t-butyldiphenylsiloxy)-3-(4-pyridyl)propionitrile (1.00 g, 2.59 mmol) in anhydrous diethyl ether (15 ml) was added dropwise to the suspension under ice-cooling with stirring over eight minutes, and the mixture was stirred at room temperature for 75 minutes. Ethyl acetate (15 ml) was added to the reaction mixture under ice-cooling, water (0.28 ml), a 15% aqueous sodium hydroxide solution (0.28 ml) and water (0.85 ml) were added thereto successively, and the whole was stirred at room temperature for 10 minutes. The reaction mixture was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the target compound (180.0 mg, yellow oily matter, 17.8%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature for 75 minutes
  3. temperaturecooling
  4. stirringsuccessively, and the whole was stirred at room temperature for 10 minutes
  5. dry with materialThe reaction mixture was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. customto give the target compound (180.0 mg, yellow oily matter, 17.8%)

Quellen und Nachweise

ORD-Eintrag
ord-e1396d93e9d0446f8ff1ba7a7f83be1d
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07741346B2

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