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

HRID 1582875Notes

Reaction equation

HRID 1582875 reaction equation
C[Sn](C)(C)[C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]([O:12][CH3:13])=[C:5]([O:14][CH3:15])[CH:4]=1.[C:18]([O:21][CH2:22][CH3:23])(=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>[CH3:13][O:12][C:6]1[C:5]([O:14][CH3:15])=[CH:4][C:3]([C:3]2[CH:4]=[C:5]3[C:6](=[CH:7][CH:8]=2)[CH:23]=[C:22]([O:21][CH3:18])[C:22]([O:21][CH3:18])=[CH:23]3)=[C:8]([N+:9]([O-:11])=[O:10])[CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 10759980Trimethyl(3,4-dimethoxy-6-nitrophenyl)stannane

Product 1

HCID 227164246-(4,5-Dimethoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Tetrakis(triphenylphosphine)palladium(0) (80 mg) and cuprous bromide (16 mg) were added to a solution of 6,7-dimethoxy-2-naphthalenetriflate (10, 220 mg, 0.655 mmol) and trimethyl(3,4-dimethoxy-6-nitrophenyl)stannane (16, 220 mg, 0.64 mmol) in THF (25 mL). The mixture was stirred at room temperature for 0.5 h., and then refluxed under nitrogen for 32 hr. 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 60:40 hexanes:ethyl acetate to give compound 17; 1H NMR (CDCl3) d 3.95(3H, s), 3.99(6H, s), 4.01(3H, s), 6.86(1H, s), 7.12(1H, s), 7.14(1H, s), 7.23(1H, dd, J=8.4, J=1.8), 7.56(1H, s), 7.61(1H, d, J=1.7), 7.70(1H, d, J=8.4); 13C NMR d 56.4, 56.9, 106.7, 107.0, 108.3, 114.4, 124.9, 125.7, 127.0, 129.0, 129.5, 132.2, 134.6, 141.6, 148.4, 150.4, 152.7.

Workup

  1. temperaturerefluxed under nitrogen for 32 hr
  2. temperatureAfter Cooling
  3. washwas 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 60:40 hexanes

Sources & evidence

ORD record
ord-264075b1c6594781b4de7373ee7cefe6
Source dataset
uspto-grants-2004_05
Patent number
US06740650B2

Reaction notes

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