Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannane → 7-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene

HRID 1582893ノート

反応式

HRID 1582893 の反応式
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][C:9](OS(C(F)(F)F)(=O)=O)=[CH:10]2)=[CH:5][CH:4]=1.C[Sn](C)(C)[C:23]1[C:28]([N+:29]([O-:31])=[O:30])=[CH:27][C:26]2[O:32][CH2:33][O:34][C:25]=2[CH:24]=1>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>[CH2:33]1[O:34][C:25]2[C:26](=[CH:27][C:28]([N+:29]([O-:31])=[O:30])=[C:23]([C:9]3[CH:10]=[C:11]4[C:6]([CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:12]4)=[CH:7][CH:8]=3)[CH:24]=2)[O:32]1

参加物

5

反応物 2

HCID 10782610Trimethyl(3,4-methylenedioxy-6-nitrophenyl)stannaneHCID 10892112Methanesulfonic acid, trifluoro-, 7-methoxy-2-naphthalenyl ester

生成物 1

HCID 227164227-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene収率 34%

試薬・触媒・溶媒 2

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

実験手順

Tetrakis(triphenylphosphine)palladium (0) (120 mg) and cuprous bromide (20 mg) were added to a solution of 7-Methoxy-2-trifluoromethanesulfonyloxynaphthalene 47 (336 mg, 1.1 mmol) and trimethylnitroarylstannane 62 (300 mg, 0.92 mmol) in THF (30 mL) at room temperature and stirred for 0.5 h. The mixture was then refluxed under N2 overnight. After cooling, THF was evaporated in vacuo and ethyl acetate (30 mL) was added to the residue. The solution was washed with water. 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 evaporated in vacuo. The residue was chromatographed using a 80:20 mixture of hexanes:ethyl acetate to give 48 (100 mg) in 34% yield; IR (KBr) 2915, 1627, 1509, 1481, 1425, 1333, 1262, 1218 cm−1; 1H NMR (CDCl3) δ3.92 (3H, s), 6.15 (2H, s), 6.88 (1H, s), 7.13-7.23 (3H, m), 7.48 (1H, s), 7.64 (1H, s), 7.74-7.81 (2H, m); 13C NMR δ55.81, 103.47, 105.90, 106.46, 111.60, 119.84, 124.13, 126.07, 128.50, 128.72, 129.75, 133.89, 134.97, 136.60, 143.42, 147.63, 151.45, 158.61; HRMS (EI) calcd for C18H13NO5 m/z: 323.0794; found: 323.0787.

後処理

  1. temperatureThe mixture was then refluxed under N2 overnight
  2. temperatureAfter cooling
  3. customTHF was evaporated in vacuo and ethyl acetate (30 mL)
  4. additionwas added to the residue
  5. washThe solution was washed with water
  6. customThe organic layer was separated
  7. customto remove
  8. washThe organic layer was then washed with brine
  9. dry with materialdried (anhydrous Na2SO4)
  10. customevaporated in vacuo
  11. customThe residue was chromatographed
  12. additiona 80:20 mixture of hexanes

出典と根拠

ORDレコード
ord-84965191ddc641e893d486bff2090e79
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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