反応 #5486

反応方程式

ammonium hydroxide

Methanesulfonic acid

2-Ethoxycarbonyl-cyclononanone

sodium azide

→

ethyl 2-oxo-1-azacyclodecane-10-carboxylate

溶媒

chloroform

反応条件

後処理

1. 1
   温度heated
2. 2
   温度to reflux for 4 hours
3. 3
   workup.ADDITIONThe reaction mixture is poured onto ice
4. 4
   抽出extracted several times with methylene chloride
5. 5
   乾燥The combined organic layers are dried (MgSO4)
6. 6
   その他the solvent is evaporated
7. 7
   その他The product is purified by silica gel chromatography (40% ethyl acetate/hexane)

実験手順

2-Ethoxycarbonyl-cyclononanone (13.72 g, 64.7 mmol) is dissolved in chloroform (200 mL) and cooled to 0° C. Methanesulfonic acid (62.4 g, 650 mmol) is added, followed by sodium azide (12.68 g, 195 mmol). The reaction is stirred at room temperature for 30 minutes, and then heated to reflux for 4 hours. The reaction mixture is poured onto ice, made basic with concentrated ammonium hydroxide (pH=9), and extracted several times with methylene chloride. The combined organic layers are dried (MgSO4), and the solvent is evaporated. The product is purified by silica gel chromatography (40% ethyl acetate/hexane) to give ethyl 2-oxo-1-azacyclodecane-10-carboxylate, m.p. 101°-103° C.

出典