Reaktion #945752

Reaktionsgleichung

3-(4-methoxyphenyl)propionic acid

N,O-dimethylhydroxylamine hydrochloride

EDC

triethylamine

→

oil

Ausbeute 85.5%

N-Methoxy-3-(4-methoxy-phenyl)-N-methyl-propionamide

Ausbeute 85.5%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated
2. 2
   SonstigeThe residue was partitioned between 1 N HCl and EtOAc
3. 3
   WaschenThe organic layers were washed with saturated NaHCO3, brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Einengenconcentrated to an oil
6. 6
   SonstigeThe oil was purified by silica gel chromatography (40% EtOAc in hexanes)

Vorschrift

N,O-dimethylhydroxylamine hydrochloride (5.41 g, 55.5 mmol), EDC (12.77 g, 66.6 mmol), followed by triethylamine (17 mL, 122 mmol) were added to a cooled 0° C. solution of 3-(4-methoxyphenyl)propionic acid (10 g, 55.5 mmol). The reaction mixture was stirred for 15 h under N2 and then concentrated. The residue was partitioned between 1 N HCl and EtOAc. The organic layers were washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated to an oil. The oil was purified by silica gel chromatography (40% EtOAc in hexanes) to give a clear oil (10.6 g, 85%).

Quelle