Reaction #74254

Reaction equation

8,8-dibromobicyclo[5.1.0]octane

methyl glycolate

aluminum

→

17

Yield 66.0%

methyl 2-bromocyclooct-1-en-3-glycolate

Yield 66.0%

Solvents

toluene

Conditions

Workup

1. 1
   Filtrationthe silver salts are filtered off through a sintered glass funnel
2. 2
   Washwashed with AcOEt
3. 3
   ConcentrationThe solution is concentrated under vacuum
4. 4
   Otherto give a viscous brown oil which
5. 5
   Otheris purified by chromatography on silica gel (cyclohexane/2-15% AcOEt)

Procedure

3.85 g of silver perchlorate (18.6 mmol) are added to a solution of 8,8-dibromobicyclo[5.1.0]octane 16 (2.5 g, 9.3 mmol) and methyl glycolate (6.35 ml, 83.9 mmol) dissolved in 5 ml of anhydrous toluene in a dry round-bottomed flask under Ar protected from light by an aluminum film. The reaction mixture is stirred at ambient temperature for 1 h 30 and then the silver salts are filtered off through a sintered glass funnel and washed with AcOEt. The solution is concentrated under vacuum to give a viscous brown oil which is purified by chromatography on silica gel (cyclohexane/2-15% AcOEt) to produce 17 in the form of a yellow oil (w=1.7 g, i.e. 66% yield).

Source