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

HRID 1166742ノート

反応式

HRID 1166742 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-ae5062cc5897487ab8c327f54d0e14e1
出典データセット
uspto-grants-2003_09
特許番号
US06613942B1

反応ノート

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