Sulfuric acid magnesium salt (1:1) → 2-[4-(Benzyloxy)-3-bromobenzyl]azulene

HRID 1375988Notes

Reaction equation

HRID 1375988 reaction equation
N1[CH2:5][CH2:4][CH2:3][CH2:2]1.S([O-])([O-])(=O)=O.[Mg+2].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([CH3:29])=O)=[CH:22][C:21]=1[Br:30])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(OCC)C>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]2[CH:5]=[C:4]3[C:2](=[CH:3][CH:4]=[CH:5][CH:2]=[CH:3]3)[CH:29]=2)=[CH:22][C:21]=1[Br:30])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 31268PyrrolidineHCID 230805631-[3-Bromo-4-(phenylmethoxy)phenyl]-2-propanone

Product 1

HCID 587861482-[4-(Benzyloxy)-3-bromobenzyl]azulene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Pyrrolidine (1.9 ml) and magnesium sulfate (2.74 g) were added to a solution of 1-[4-(benzyloxy)-3-bromophenyl]acetone (3.65 g) in diethyl ether (30 ml) and the mixture was stirred at room temperature for 12 hours. After filtration, the solvent was evaporated under reduced pressure. The resulting residue was dried under reduced pressure and dissolved in ethanol (30 ml). 2H-cyclohepta[b]furan-2-on (0.5 g) was added to the solution and the mixture was refluxed with heating for eight hours. The reaction mixture was concentrated. The resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane) to obtain 2-[4-(benzyloxy)-3-bromobenzyl]azulene (0.84 g).

Workup

  1. filtrationAfter filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was dried under reduced pressure
  4. dissolutiondissolved in ethanol (30 ml)
  5. addition2H-cyclohepta[b]furan-2-on (0.5 g) was added to the solution
  6. temperaturethe mixture was refluxed
  7. temperaturewith heating for eight hours
  8. concentrationThe reaction mixture was concentrated
  9. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-05f313adf1594475af3041ceb4cb81e2
Source dataset
uspto-grants-2007_01
Patent number
US07169761B2

Reaction notes

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