3,5-Di-tert-butylphenol → 2-(1-Aminoethyl)-3,5-di-tert-butylphenol

HRID 1173305

Reaktionsgleichung

Reaktionsgleichung von HRID 1173305
[C:1]([C:5]1[CH:6]=[C:7]([OH:15])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(O[CH:20]([NH:22]C(=O)C)[CH3:21])(C)C>FC(F)(F)C(O)=O>[NH2:22][CH:20]([C:8]1[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[OH:15])[CH3:21]

Komponenten

4

Edukt 2

HCID 708253,5-Di-tert-butylphenolHCID 14204909N-(1-Isopropoxyethyl)acetamide

Produkt 1

HCID 104672612-(1-Aminoethyl)-3,5-di-tert-butylphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

To a solution of 2.06 g (10.0 mmol) of 3,5-di-tert-butylphenol in 10 mL of trifluoroacetic acid was added 1.6 g (11.0 mmol) of N-(1-isopropoxyethyl)acetamide and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo, and the residue was partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layers were separated and then extracted with EtOAc. The organic layers were combined, dried (Na2SO4), filtered and evaporated in vacuo. The product was purified on a silica gel flash chromatography column eluted with 0-25% EtOAc in CH2Cl2. Evaporation of the purified fraction and drying in vacuo afforded the title compound.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. customThe aqueous layers were separated
  4. extractionextracted with EtOAc
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe product was purified on a silica gel flash chromatography column
  9. washeluted with 0-25% EtOAc in CH2Cl2
  10. customEvaporation of the purified fraction
  11. customdrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-ad47a43033f5478db11c66aea3474bbe
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834062B2

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