Ethyl Acetate → HCID 12136644, Verbindung

HRID 11460

Reaktionsgleichung

Reaktionsgleichung von HRID 11460
[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

Komponenten

7

Edukt 4

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

Produkt 1

HCID 12136644HCID 12136644, VerbindungAusbeute 17,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Lithium aluminum hydride (299 mg, 7.87 mmol) was suspended in anhydrous diethyl ether (10 ml) under a nitrogen atmosphere, and 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. The temperature was raised to room temperature, and the mixture was stirred for 75 minutes. The reaction mixture was cooled with ice, ethyl acetate (15 ml) was added to the reaction mixture, and water (0.28 ml), a 15% aqueous sodium hydroxide solution (0.28 ml) and water (0.85 ml) were added thereto successively. The temperature was raised to room temperature, and the whole was stirred 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 titled compound (180.0 mg, yellow oily matter, 17.8%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was stirred for 75 minutes
  3. temperatureThe temperature was raised to room temperature
  4. stirringthe whole was stirred 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

Quellen und Nachweise

ORD-Eintrag
ord-f849e22082904606b4e01986dc77a519
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098226B2

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