Ethyl Acetate → Tert-butyl N-[2-(2-hydroxyethyl)phenyl]carbamate

HRID 1244494Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1244494
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12](CC(O)=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:25](OCC)(=[O:27])[CH3:26]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[CH2:26][CH2:25][OH:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 28249932-(4-((Tert-butoxycarbonyl)amino)phenyl)acetic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10752353Tert-butyl N-[2-(2-hydroxyethyl)phenyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

4-(t-butoxycarbonylamino)-benzeneacetic acid (2.9 g, 11.4 mmoles) is dissolved in 10 ml of anhydrous THF at 0° C. and added to a suspension of LiAlH4 (0.52 g, 13.6 mmoles) in 30 ml of THF. The reaction mixture is agitated at ambient temperature for 1.5 hours. 50 ml of ethyl acetate then 20 ml of 2 N soda are added to the medium. The expected product is extracted from the organic phase, which is then washed with 3 times 15 ml of water. The organic phase is dried and the solvent evaporated off under reduced pressure. Then the reaction product is purified on silica gel in a dichloromethane/methanol mixture (95/5). 1.1 g (40%) is thus obtained in the form of a colourless oil.

Aufarbeitung

  1. extractionThe expected product is extracted from the organic phase, which
  2. washis then washed with 3 times 15 ml of water
  3. customThe organic phase is dried
  4. customthe solvent evaporated off under reduced pressure
  5. customThen the reaction product is purified on silica gel in a dichloromethane/methanol mixture (95/5)
  6. custom1.1 g (40%) is thus obtained in the form of a colourless oil

Quellen und Nachweise

ORD-Eintrag
ord-a5d074ac3a9b4ce8adf5df15d53b4303
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07122535B2

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