Methyl Glycolate → Methyl 2-bromocyclooctene-3-glycolate

HRID 2047951Notes

Reaction equation

HRID 2047951 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 65%

Reagents, catalysts & solvents 2

HCID 24562Silver perchlorateCatalystHCID 1140TolueneSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-aecca29ee881433da6100cd2b5476ea6
Source dataset
uspto-grants-2013_11
Patent number
US08592619B2

Reaction notes

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