反応 #48452

反応方程式

2-bromoethyl methyl ether

Cesium carbonate

5-bromo-3-nitropyridin-2-ol

2-bromoethyl methyl ether

water

→

title compound

収率 58.4%

5-Bromo-1-(2-methoxyethyl)-3-nitropyridin-2(1H)-one

収率 58.4%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   workup.WAITAfter 4 h
2. 2
   抽出The mixture was extracted with ethyl acetate (3×)
3. 3
   洗浄the combined organic extracts were washed with saturated brine
4. 4
   乾燥dried over sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   その他Purification by silica gel chromatography (100% hexanes→40% ethyl acetate/hexanes)

実験手順

Cesium carbonate (14.88 g, 45.66 mmol) was added to a solution of 5-bromo-3-nitropyridin-2-ol (10.0 g, 45.7 mmol) and 2-bromoethyl methyl ether (4.29 mL, 45.66 mmol) in N,N-dimethylformamide (400 mL). After 3 h, additional 2-bromoethyl methyl ether (4.29 mL, 45.7 mmol) was added, and the reaction was heated to 60° C. After 4 h, water was added. The mixture was extracted with ethyl acetate (3×), and the combined organic extracts were washed with saturated brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→40% ethyl acetate/hexanes) gave the title compound (7.39 g). MS 277 (M).

出典