Reacción #1869216

Ecuación de reacción

N2

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

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

Cesium carbonate

→

crude product

Rendimiento 122.2%

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

Rendimiento 122.2%

Disolventes

DMF

water

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   LavadoThe organic phase was washed with water (3×250 mL)
2. 2
   Secadodried over Na2SO4
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated in vacuo

Procedimiento

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, 0.11 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 (63%).

Fuente