Reaktion #161260

Reaktionsgleichung

methyl 2-tert-butyl-5-aminobenzoate

LiAlH4

→

(2-tert-butyl-5-aminophenyl)methanol

Ausbeute 20.0%

Lösungsmittel

H2O

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was refluxed for 2 h
2. 2
   Extraktionextracted with EtOAc
3. 3
   WaschenThe combined organic layers were washed with brine
4. 4
   Trocknendried over MgSO4
5. 5
   FiltrationAfter filtration
6. 6
   Einengenthe filtrate was concentrated

Vorschrift

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).

Quelle