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Lithium Chloride → 2-Phenyl-3-methyl-8-vinylquinoline

HRID 1167179
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인쇄 미리보기

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HRID 1167179 반응식
[Cl-].[Li+].[CH2:3](C([Sn])=C(CCCC)CCCC)[CH2:4]CC.[C:18]1([C:24]2[C:33]([CH3:34])=[CH:32][C:31]3[C:26](=[C:27](OS(C(F)(F)F)(=O)=O)[CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>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>[C:18]1([C:24]2[C:33]([CH3:34])=[CH:32][C:31]3[C:26](=[C:27]([CH:3]=[CH2:4])[CH:28]=[CH:29][CH:30]=3)[N:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1
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참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 155214792-Phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinolineHCID 53438229Tri(butyl)vinyltin

생성물 1

HCID 229959252-Phenyl-3-methyl-8-vinylquinoline수율 96%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매
HCID 31275
1,4-Dioxane
용매

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온도
110 °C

실험 절차

6.3 g (150 mmol) of lithium chloride, 16.8 ml (57 mmol) of tributylvinyltin and 1.6 g (1.5 mmol) of Pd(PPh3)4 are added sequentially at ambient temperature to a solution of 17.7 g (48 mmol) of 2-phenyl-3-methyl-8-trifluoromethanesulfonyloxyquinoline in 250 ml of dioxane, degassed beforehand using a stream of nitrogen. The reaction medium is then heated at 110° C. for 16 hours. After evaporating the dioxane, the residue is taken up in 200 ml of water and 200 ml of ethyl acetate. The aqueous phase is extracted with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7) to provide 11.3 g of 2-phenyl-3-methyl-8-vinylquinoline in the form of a colorless oil. (Yield: 96%)

후처리

  1. customdegassed
  2. customAfter evaporating the dioxane
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue is purified by silica gel chromatography (eluent: ethyl acetate/cyclohexane 3/7)

출처 및 근거

ORD 기록
ord-3b7055f1a163408db7d21a694642bc11
출처 데이터셋
uspto-grants-2003_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06617336B1

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