反応 #1869216

反応方程式

N2

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

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

Cesium carbonate

→

crude product

収率 122.2%

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

収率 122.2%

溶媒

DMF

water

ethyl acetate

反応条件

後処理

1. 1
   洗浄The organic phase was washed with water (3×250 mL)
2. 2
   乾燥dried over Na2SO4
3. 3
   ろ過filtered
4. 4
   濃縮concentrated in vacuo

実験手順

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%).

出典