반응 #328661

반응 방정식

8,8-dibromobicyclo[5.1.0]octane

methyl glycolate

aluminium

→

methyl 2-bromocyclooctene-3-glycolate

수율 65.0%

용매

toluene

반응 조건

후처리

1. 1
   여과the silver salts are filtered over a frit
2. 2
   세척washed with AcOEt
3. 3
   농축The solution is concentrated under vacuum
4. 4
   기타to give a viscous brown oil which
5. 5
   기타is purified by silica gel chromatography (2-15% AcOEt in cyclohexane)
6. 6
   기타to obtain the product in the form of a yellow oil

실험 절차

Added to a solution of 8,8-dibromobicyclo[5.1.0]octane (2.5 g i.e. 9.3 mmol) and methyl glycolate (6.35 ml, i.e. 83.9 mmol) dissolved in 5 ml of anhydrous toluene in a dry round-bottomed flask, under Ar and protected from the light by aluminium foil, are 3.85 g of silver perchlorate (i.e. 18.6 mmol). The reaction is stirred for 1 h 30 min at room temperature, then the silver salts are filtered over a frit and washed with AcOEt. The solution is concentrated under vacuum to give a viscous brown oil which is purified by silica gel chromatography (2-15% AcOEt in cyclohexane) to obtain the product in the form of a yellow oil having a mass m=1.6 g, i.e. 65% yield.

출처