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

HRID 1582875ノート

反応式

HRID 1582875 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-264075b1c6594781b4de7373ee7cefe6
出典データセット
uspto-grants-2004_05
特許番号
US06740650B2

反応ノート

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