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

HRID 990761

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HRID 990761 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

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 preci-pitated as a light yellow solid (2.46 g, 54%): 1H NMR (DMSO-d6) δ7.89(d,2H), 7.15(d,2H), 5.45(hept, 1H), 3.82(s,3H), 1.48(d,6H).

후처리

  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

출처 및 근거

ORD 기록
ord-61e2580eba0e481ab3e0de323c080694
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06462059B1

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