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

HRID 85200노트

반응식

HRID 85200 반응식
Br[C:2]1[C:3](=[O:18])[N:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[CH3:17])[CH:5]=[CH:6][CH:7]=1.[CH2:19](C([Sn])=C(CCCC)CCCC)[CH2:20]CC>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:17][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:19]=[CH2:20])[C:3]1=[O:18]

참가 물질

5

반응물 2

HCID 53438229Tri(butyl)vinyltinHCID 594101573-Bromo-1-(2-methyl-4-nitrophenyl)pyridin-2(1H)-one

생성물 1

HCID 594101981-(2-Methyl-4-nitrophenyl)-3-vinylpyridin-2(1H)-one

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

50 g (162 mmol) of the compound from Example 12A are dissolved in 700 ml of anhydrous dioxane, 62 g (194 mmol) of tributylvinyltin and 4.7 g (4 mmol) of tetrakis(triphenylphosphine)palladium are added and the mixture is heated at reflux for 15 h. The mixture is allowed to cool and filtered through kieselguhr. The filter cake is washed with ethyl acetate and the combined filtrates are evaporated to dryness under reduced pressure. The residue is applied to silica gel and chromatographed on 800 g of silica gel using a gradient of cyclohexane and ethyl acetate. This gives 27 g (62% of theory) of the desired product.

후처리

  1. temperaturethe mixture is heated
  2. temperatureat reflux for 15 h
  3. temperatureto cool
  4. filtrationfiltered through kieselguhr
  5. washThe filter cake is washed with ethyl acetate
  6. customthe combined filtrates are evaporated to dryness under reduced pressure
  7. customchromatographed on 800 g of silica gel using a gradient of cyclohexane and ethyl acetate

출처 및 근거

ORD 기록
ord-bebb55d16b064ec6ae4a18aa30f97e3d
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846934B2

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