Tri(butyl)vinyltin → 1-(2-Methoxy-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

HRID 452222노트

반응식

HRID 452222 반응식
Br[C:2]1[C:3](=[O:19])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[O:17][CH3:18])[CH:5]=[CH:6][CH:7]=1.[CH2:20](C([Sn])=C(CCCC)CCCC)[CH2:21]CC>O1CCOCC1>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH:20]=[CH2:21])[C:3]1=[O:19]

참가 물질

4

반응물 2

HCID 53438229Tri(butyl)vinyltinHCID 594101453-Bromo-1-(2-methoxy-4-nitrophenyl)pyridin-2(1H)-one

생성물 1

HCID 594101761-(2-Methoxy-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

100 g (308 mmol) of the compound from Example 28A are dissolved in 1.4 l of anhydrous dioxane, and 8.9 g (7.7 mmol) of tetrakis(triphenylphospine)palladium and 117 g (370 mmol) of tributylvinyltin are added. The mixture is heated at reflux for 16 h. The reaction solution is then allowed to cool and filtered through kieselguhr. The filtrates are concentrated to dryness under reduced pressure. The residue is chromatographed on silica gel using a gradient of cyclohexane and ethyl acetate. The product-containing fractions are combined and concentrated to dryness under reduced pressure. Petroleum ether is added until crystallization sets in. The crystals are filtered off and dried under reduced pressure. This gives 37 g (41% of theory) of the desired product.

후처리

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 16 h
  3. temperatureto cool
  4. filtrationfiltered through kieselguhr
  5. concentrationThe filtrates are concentrated to dryness under reduced pressure
  6. customThe residue is chromatographed on silica gel using a gradient of cyclohexane and ethyl acetate
  7. concentrationconcentrated to dryness under reduced pressure
  8. additionPetroleum ether is added until crystallization sets in
  9. filtrationThe crystals are filtered off
  10. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-327289a083b04419be65ffcc192100fd
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487111B2

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