Methyl Acrylate → (E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate

HRID 55258

反応式

HRID 55258 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([O:14][C:15]1[C:16](I)=[N:17][CH:18]=[CH:19][CH:20]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:22][O:23][C:24](=[O:27])[CH:25]=[CH2:26]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:22][O:23][C:24](=[O:27])/[CH:25]=[CH:26]/[C:16]1[C:15]([O:14][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

参加物

7

反応物 3

HCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 199575013-Benzyloxy-2-iodopyridine

生成物 1

HCID 22161738(E)-Methyl 3-[3-(phenylmethoxy)pyridin-2-yl]-2-propenoate

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

5.2 g of palladium(II) acetate, 77.8 g of potassium carbonate and 72.5 g of tetrabutylammonium bromide are added to a solution of 70 g of 3-benzyloxy-2-iodopyridine and 39.8 ml of acrylic acid methyl ester in 120 ml of dimethylformamide, and the suspension is stirred under argon atmosphere for 10 hours at 100° C. (bath temperature). The reaction mixture is concentrated by evaporation in a vacuum, the residue is added to water and shaken out with ethyl acetate. The organic phase is washed three times with water and once with saturated common salt solution, dried with sodium sulfate and concentrated by evaporation. The crude product is chromatographed on silica gel with hexane/10-25% ethyl acetate. 48.2 g of 3-(3-benzyloxy-2-pyridyl)-(2E)-2-propenoic acid methyl ester is obtained as oil.

後処理

  1. concentrationThe reaction mixture is concentrated by evaporation in a vacuum
  2. additionthe residue is added to water
  3. stirringshaken out with ethyl acetate
  4. washThe organic phase is washed three times with water
  5. dry with materialonce with saturated common salt solution, dried with sodium sulfate
  6. concentrationconcentrated by evaporation
  7. customThe crude product is chromatographed on silica gel with hexane/10-25% ethyl acetate

出典と根拠

ORDレコード
ord-d4846378d04a4d3fb9385b65082d0c14
出典データセット
uspto-grants-1997_04
特許番号
US05624943

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