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

HRID 452222

反応式

HRID 452222 の反応式
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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-327289a083b04419be65ffcc192100fd
出典データセット
uspto-grants-2013_07
特許番号
US08487111B2

関連ノート

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