Methyl Glycolate → Methyl 2-bromocyclooctene-3-glycolate

HRID 45976

Reaction equation

HRID 45976 reaction equation
Br[C:2]1([Br:10])[CH:9]2[CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]2.[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][OH:13].[Al]>C1(C)C=CC=CC=1.Cl([O-])(=O)(=O)=O.[Ag+]>[Br:10][C:2]1[CH:3]([CH:12]([OH:13])[C:11]([O:15][CH3:16])=[O:14])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]=1

Participants

6

Reactant 3

HCID 66774Methyl GlycolateHCID 5359268AluminumHCID 127597888,8-Dibromobicyclo[5.1.0]octane

Product 1

HCID 66746412Methyl 2-bromocyclooctene-3-glycolateYield 66%

Reagents, catalysts & solvents 2

HCID 24562Silver perchlorateCatalystHCID 1140TolueneSolvent

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).

Workup

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

Sources & evidence

ORD record
ord-ffac2490fbc3456483c73090f1c31fd7
Source dataset
uspto-grants-2013_09
Patent number
US08541604B2

Linked notes

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