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

HRID 55258

반응식

HRID 55258 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d4846378d04a4d3fb9385b65082d0c14
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05624943

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