Aluminium lithium hydride → (2-Tert-butyl-5-aminophenyl)methanol

HRID 401410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 401410
[C:1]([C:5]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:6]=1[C:7](OC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.O>[C:1]([C:5]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:6]=1[CH2:7][OH:8])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 57470263Methyl 2-tert-butyl-5-aminobenzoate

Produkt 1

HCID 57567299(2-Tert-butyl-5-aminophenyl)methanolAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of methyl 2-tert-butyl-5-aminobenzoate (159 mg, 0.72 mmol) in THF (5 mL) was added dropwise LiAlH4 (1.4 mL, 1M in THF, 1.4 mmol) at 0° C. The reaction mixture was refluxed for 2 h, diluted with H2O and extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. After filtration, the filtrate was concentrated to give (2-tert-butyl-5-aminophenyl)methanol (E-8) (25 mg, 20%), which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.17 (d, J=8.5 Hz, 1H), 6.87 (d, J=2.6 Hz, 1H), 6.56 (dd, J=8.4, 2.7 Hz, 1H), 4.83 (s, 2H), 1.36 (s, 9H).

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 2 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-76b5339337624f199bae42f220f385e2
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08741925B2

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