反応 #2146688

反応方程式

sodium methoxide methanol

2-bromo-3-hydroxypyridine

methyl iodide

→

2-bromo-3-methoxypyridine

溶媒

dimethylsulfoxide

反応条件

後処理

1. 1
   workup.DISTILLATIONto distill off methanol
2. 2
   温度After the reaction solution was cooled down to 5° C.
3. 3
   その他After the completion of the reaction
4. 4
   抽出extracted twice with chloroform
5. 5
   洗浄The combined chloroform layer was washed with a 1 mol/L sodium hydroxide solution
6. 6
   洗浄washed twice with a saturated sodium chloride solution
7. 7
   乾燥dried over anhydrous sodium sulfate
8. 8
   workup.DISTILLATIONAfter the solvent was distilled off under reduced pressure

実験手順

31.11 g (corresponding to 178.88 mmol) of 2-bromo-3-hydroxypyridine was dissolved in 95.8 mL of dimethylsulfoxide, and 89.9 mL (corresponding to 89.9 mmol) of a 1 mol/L sodium methoxide-methanol solution was added thereto. Then, the reaction solution was heated to 90° C. to distill off methanol. After the reaction solution was cooled down to 5° C. or lower, 29.2 g (corresponding to 205.62 mmol) of methyl iodide was added, and then stirred at room temperature for 17 hours. After the completion of the reaction, the reaction solution was poured into ice-water and extracted twice with chloroform. The combined chloroform layer was washed with a 1 mol/L sodium hydroxide solution, washed twice with a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, 20.74 g (corresponding to 110.31 mmol) of 2-bromo-3-methoxypyridine was obtained (FIG. 3, Step 1).

出典