Reaktion #52066

Reaktionsgleichung

[3-(hydroxyimino-methyl)-phenoxy]-acetic acid tert-butyl ester

Ammonium hydroxide

→

title compound

(3-Aminomethyl-phenoxy)-acetic acid tert-butyl ester

Lösungsmittel

EtOH

ethanol

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe catalyst was removed via filtration through Celite® (diatomaceous earth)
2. 2
   Einengenthe solution was concentrated to a clear oil
3. 3
   SonstigePurification via flash chromatography on silica gel (96.5/3.5/0.1 to 9/1/0.1 CH2Cl2/MeOH/NH4OH)

Vorschrift

To a solution of [3-(hydroxyimino-methyl)-phenoxy]-acetic acid tert-butyl ester (2.25 g, 5.96 mmol) in EtOH (10 mL) was added Raney Nickel (about 1 g, washed with water followed by EtOH) in 100 mL ethanol. Additional EtOH (90 mL) was required for the transfer. Ammonium hydroxide (10 mL) was added and the mixture was shaken under 45 psi of H2 for 4 hours. The catalyst was removed via filtration through Celite® (diatomaceous earth) and the solution was concentrated to a clear oil. Purification via flash chromatography on silica gel (96.5/3.5/0.1 to 9/1/0.1 CH2Cl2/MeOH/NH4OH) afforded the title compound as a yellow oil. 1H NMR (400 MHz, CDCl3) δ 7.23 (m, 1H), 6.92 (m, 2H), 6.72 (d, 1H), 4.50 (s, 2H), 3.82 (s, 2H), 1.96 (m, 2H), 1.46 (s, 9H); MS 238 (M+1).

Quelle