反応 #88662

反応方程式

3-(5-bromo-2-furyl)acryloyl azide

diphenyl ether

tributylamine

→

title compound

2-Bromofuro[3,2-c]pyridin-4(5H)-one

溶媒

tert-butyl methyl ether

反応条件

後処理

1. 1
   温度to cool to room temperature
2. 2
   ろ過The resulting solid was collected by filtration
3. 3
   その他The obtained solid was purified by silica gel column chromatography (hexane
4. 4
   workup.ADDITIONTo the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution
5. 5
   抽出the mixture was extracted with ethyl acetate
6. 6
   乾燥The extract was dried over anhydrous magnesium sulfate
7. 7
   濃縮concentrated in vacuo
8. 8
   その他recrystallized from ethyl acetate

実験手順

A mixture of 3-(5-bromo-2-furyl)acryloyl azide (20.7 g), diphenyl ether (200 mL) and tributylamine (16 mL) was stirred at 220-230° C. for 30 min under a nitrogen atmosphere. The reaction mixture was allowed to cool to room temperature, and tert-butyl methyl ether (200 mL) was added thereto. The resulting solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (hexane, then ethyl acetate/THF), followed by HPLC (C18, mobile phase: water/acetonitrile (including 0.1% TFA)). To the obtained fraction was added a saturated aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, concentrated in vacuo, and recrystallized from ethyl acetate to give the title compound (7.00 g) as a white solid.

出典