Reaktion #357240

Reaktionsgleichung

N2

N-(2-Hydroxy-4-methoxyphenyl)acetamide

(2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate

Cesium carbonate

→

crude product

Ausbeute 122.2%

N-{4-Methoxy-2[(2S)-oxiran-2-ylmethoxy]phenyl}acetamide

Ausbeute 122.2%

Lösungsmittel

DMF

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe organic phase was washed with water (3×250 mL)
2. 2
   Trocknendried over Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated in vacuo

Vorschrift

N-(2-Hydroxy-4-methoxyphenyl)acetamide (18.12 g, 0.1 mol) and (2S)-oxiran-2-ylmethyl-3-nitrobenzenesulfonate (25.92 g, 0.1 mol) were dissolved in dry DMF (75 mL) and stirred under nitrogen (N2) on an ice-bath. Cesium carbonate (35.8 g, 0.1 mol) was added and the stirring under N2 was continued at ambient temperature overnight. The mixture was poured into ethyl acetate (1 L) and water (250 mL). The organic phase was washed with water (3×250 mL), dried over Na2SO4, filtered and concentrated in vacuo to give an orange solid crude product (29 g), which was recrystallized from ethanol (100 mL) and washed with ether to give white crystals. More white crystals were obtained from the mother liquor, after evaporation and recrystillazition from 2-propanol. Total yield 15 g is (63%).

Quelle