Methane → 3-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

HRID 843035

反応式

HRID 843035 の反応式
[CH:1]([O:4][C:5]1[C:6](=[O:23])[C:7](=[O:22])[C:8]=1[Sn](CCCC)(CCCC)CCCC)([CH3:3])[CH3:2].I[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1.C(OCC)C.C>CN(C)C=O.C(OCC)(=O)C>[CH:1]([O:4][C:5]1[C:6](=[O:23])[C:7](=[O:22])[C:8]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 297MethaneHCID 3283Diethyl EtherHCID 696764-IodoanisoleHCID 27366833-Isopropoxy-4-(tri-n-butylstannyl)-3-cyclobutene-1,2-dione

生成物 1

HCID 147378433-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-isopropoxy-4-(tri-n-butyl-stannyl)-3-cyclobutene-1,2-dione (J. Org. Chem. 1990, 55, 5359-5364) (8.00 g, 18.65 mmol) in N,N-dimethyl-formamide (40 mL) was added 4-iodoanisole (4.85 g, 20.72 mmol). The flask was purged with nitrogen and cooled to 0° C. Benzylchloro-bis-(triphenylphosphine)palladium (II) (0.942 g, 1.24 mmol) and cuprous iodide (0.355 g, 1.87 mmol) were added and the mixture was stirred at room temperature overnight. Diethylether (200 mL) was added and the mixture was washed successively with saturated aqueous ammonium chloride, 10% aqueous potassium fluoride and saturated brine. The organic phase was filtered through a plug of silica. The filtrate was dried (MgSO4) and concentrated to give crude product which was dissolved in hot ethyl acetate, decolorized (charcoal) and filtered. The filtrate was treated with hexane and allowed to cool. 3-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione precipitated as a light yellow solid (2.46 g, 54%): 1H NMR (DMSO-d6) δ 7.89(d,2H), 7.15(d,2H), 5.45(hept,1H), 3.82(s,3H), 1.48(d,6H).

後処理

  1. customThe flask was purged with nitrogen
  2. washthe mixture was washed successively with saturated aqueous ammonium chloride, 10% aqueous potassium fluoride and saturated brine
  3. filtrationThe organic phase was filtered through a plug of silica
  4. dry with materialThe filtrate was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give crude product which
  7. filtrationfiltered
  8. additionThe filtrate was treated with hexane
  9. temperatureto cool
  10. custom3-Isopropoxy-4-(4-methoxy-phenyl)-cyclobut-3-ene-1,2-dione precipitated as a light yellow solid (2.46 g, 54%)

出典と根拠

ORDレコード
ord-60165b8f3d994835aa5470d7b3a96c22
出典データセット
uspto-grants-2002_04
特許番号
US06376555B1

関連ノート

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