تفاعل #5486

معادلة التفاعل

ammonium hydroxide

Methanesulfonic acid

2-Ethoxycarbonyl-cyclononanone

sodium azide

→

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

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةto reflux for 4 hours
3. 3
   workup.ADDITIONThe reaction mixture is poured onto ice
4. 4
   استخلاصextracted several times with methylene chloride
5. 5
   تجفيفThe combined organic layers are dried (MgSO4)
6. 6
   أخرىthe solvent is evaporated
7. 7
   أخرىThe product is purified by silica gel chromatography (40% ethyl acetate/hexane)

الإجراء التجريبي

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.

المصدر