Ethyl Acetate → 6-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxynaphthalene

HRID 1582872Notes

Reaction equation

HRID 1582872 reaction equation
C[Sn](C)(C)[C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]2[O:12][CH2:13][O:14][C:5]=2[CH:4]=1.[C:17]([O:20][CH2:21][CH3:22])(=O)C>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:13]1[O:14][C:5]2[C:6](=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([C:3]3[CH:4]=[C:5]4[C:6](=[CH:7][CH:8]=3)[CH:22]=[C:21]([O:20][CH3:17])[C:21]([O:20][CH3:17])=[CH:22]4)[CH:4]=2)[O:12]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 10782610Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane

Product 1

HCID 227164206-(4,5-Methylenedioxy-2-nitrophenyl)-2,3-dimethoxynaphthalene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrakis(triphenylphosphine)palladium(0) (40 mg) and cuprous bromide (8 mg) were added to a solution of 6,7-dimethoxy-2-naphthalenetriflate (160 mg, 0.48 mmol) and trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane (8, 187 mg, 0.57 mmol) in THF (20 mL). The mixture was stirred at room temperature for 0.5 h., and then refluxed under nitrogen for 18 h. After Cooling, THF was rotaevaporated and ethyl acetate (50 ml) was added to the residue. the solution was washed with water (30 mL). The organic layer was separated and passed through a celite bed to remove suspended particles. The organic layer was then washed with brine, dried (anhydrous Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel using 70:30 hexanes:ethyl acetate to give a mixture of two compounds with same Rf value. The mixture can be separated after the hydrogenation step.

Workup

  1. temperaturerefluxed under nitrogen for 18 h
  2. temperatureAfter Cooling
  3. washthe solution was washed with water (30 mL)
  4. customThe organic layer was separated
  5. customto remove
  6. washThe organic layer was then washed with brine
  7. dry with materialdried (anhydrous Na2SO4)
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel using 70:30 hexanes
  10. customethyl acetate to give
  11. additiona mixture of two compounds with same Rf value
  12. customThe mixture can be separated after the hydrogenation step

Sources & evidence

ORD record
ord-706b38464bbe458c9fb13de40f8d4ea8
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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