Hydroquinone → 6-Methyl-5-(3-methylisoxazol-5-yl)-7,7-dimethoxy-1,2,3,4-tetrachlorobicyclo[2.2.1]hept-2-ene

HRID 354231Notes

Reaction equation

HRID 354231 reaction equation
[CH3:1][O:2][C:3]1([O:12][CH3:13])[C:7]([Cl:8])=[C:6]([Cl:9])[C:5]([Cl:10])=[C:4]1[Cl:11].C(=O)([O-])O.[Na+].[CH3:19][C:20]1[CH:24]=[C:23](/[CH:25]=[CH:26]/[CH3:27])[O:22][N:21]=1.C1(C=CC(O)=CC=1)O>C(OCC)(=O)C>[CH3:27][CH:26]1[C:4]2([Cl:11])[C:3]([O:2][CH3:1])([O:12][CH3:13])[C:7]([Cl:8])([C:6]([Cl:9])=[C:5]2[Cl:10])[CH:25]1[C:23]1[O:22][N:21]=[C:20]([CH3:19])[CH:24]=1

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 751541,2,3,4-Tetrachloro-5,5-dimethoxycyclopenta-1,3-dieneHCID 516892Sodium BicarbonateHCID 12993789trans-1-(3-Methylisoxazol-5-yl)-1-propene

Product 1

HCID 235133326-Methyl-5-(3-methylisoxazol-5-yl)-7,7-dimethoxy-1,2,3,4-tetrachlorobicyclo[2.2.1]hept-2-eneYield 44.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

1.07 g of 5,5-dimethoxy-1,2,3,4-tetrachlorocyclopenta-1,3-diene, 0.34 g of sodium hydrogen carbonate, 0.50g of trans-1-(3-methylisoxazol-5-yl)-1-propene and 0.05 g of hydroquinone were mixed and heated with stirring at 180° C. for 7 hours. The reaction solution was cooled and ethyl acetate was added. Insoluble matter was removed by filtration. Then the solvent was concentrated under reduced pressure. The obtained crude product was purified on silica gel column chromatography (elution with benzene) to give 0.70 g of the title compound as a mixture of isomers.

Workup

  1. temperatureheated
  2. temperatureThe reaction solution was cooled
  3. customInsoluble matter was removed by filtration
  4. concentrationThen the solvent was concentrated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified on silica gel column chromatography (elution with benzene)

Sources & evidence

ORD record
ord-5501bf9ea2dd4b519af242077d9fb38e
Source dataset
uspto-grants-2004_06
Patent number
US06756497B1

Reaction notes

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