반응 #2135133

반응 방정식

8,8-dibromobicyclo[5.1.0]octane

methyl glycolate

aluminum

→

methyl 2-bromocyclooctene-3-glycolate

수율 65.0%

용매

toluene

반응 조건

후처리

1. 1
   여과the silver salts are then filtered off on a sinter
2. 2
   세척washed with EtOAc
3. 3
   농축The solution is concentrated under vacuum
4. 4
   기타to give a viscous brown oil, which
5. 5
   기타is purified by chromatography on silica gel (2-150 EtOAc in cyclohexane)
6. 6
   기타to give the product in the form of a yellow oil of mass m=1.6 g, i.e. 65% yield

실험 절차

To a solution of 8,8-dibromobicyclo[5.1.0]octane (2.5 g, i.e. 9.3 mmol) and of methyl glycolate (6.32 mL, i.e. 83.9 mmol) dissolved in 5 mL of anhydrous toluene in a dry round-bottomed flask, under Ar and protected from light by a film of aluminum, are added 3.85 g of silver perchlorate (i.e. 18.6 mmol). The reaction is stirred for 1 hour 30 minutes at room temperature, and the silver salts are then filtered off on a sinter and washed with EtOAc. The solution is concentrated under vacuum to give a viscous brown oil, which is purified by chromatography on silica gel (2-150 EtOAc in cyclohexane) to give the product in the form of a yellow oil of mass m=1.6 g, i.e. 65% yield.

출처