Triethylamine → 2-[4-(2-Ethoxycarbonylvinyl)naphthyl]dioxolane

HRID 1166742노트

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HRID 1166742 반응식
FC(F)(F)S(O[C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)=[CH:9][CH:8]=1)(=O)=O.[C:24]([O:28][CH2:29][CH3:30])(=[O:27])[CH:25]=[CH2:26].C(N(CC)CC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:29]([O:28][C:24]([CH:25]=[CH:26][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]2[O:21][CH2:20][CH2:19][O:18]2)=[CH:9][CH:8]=1)=[O:27])[CH3:30]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 540831252-(4-Trifluoromethylsulfonyloxy naphthyl)dioxolane

생성물 1

HCID 536829332-[4-(2-Ethoxycarbonylvinyl)naphthyl]dioxolane수율 53.7%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
90 °C

실험 절차

Nitrogen was passed through a solution of 2-(4-trifluoromethylsulfonyloxynaphthyl) dioxolane (2.46 g, 7.06 mmol), ethyl acrylate (2.3 mL, 2.1 g, 21.2 mmol), triethylamine (4.3 g, 42.3 mmol) in DMF (6 mL) for 15 min, and bis(triphenylphosphine)palladium dichloride was added. The well stirred solution was heated at 90° C. for 8 hr, and concentrated. The residue was dissolved in ethyl acetate (50 mL), washed with brine (2×50 mL), dried (Na2SO4), and concentrated. Purification by flash chromatography using hexane/ethyl acetate 9:1 as eluent provided a yellow solid (1.13 g, 53%).

후처리

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in ethyl acetate (50 mL)
  3. washwashed with brine (2×50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customPurification by flash chromatography

출처 및 근거

ORD 기록
ord-ae5062cc5897487ab8c327f54d0e14e1
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06613942B1

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