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Water → 2-Ethenyl-5-nitropyridine

HRID 2262604
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HRID 2262604 반응식
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]([Sn](CCCC)(CCCC)C=C)[CH2:12]CC.O>C1(C)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([CH:11]=[CH2:12])=[N:3][CH:4]=1)([O-:10])=[O:9]
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참가 물질

6

반응물 3

HCID 962WaterHCID 783082-Chloro-5-nitropyridineHCID 81998Tributylvinyltin

생성물 1

HCID 230905502-Ethenyl-5-nitropyridine수율 111.6%

시약·촉매·용매 2

HCID 11776Triphenylphosphine촉매HCID 1140Toluene용매

실험 절차

0.5 g of 2-chloro-5-nitro-pyridine (3.15 mmol), 1.2 g of tributyl-vinyl-stannane (3.78 mmol), 0.036 g of tetrakistriphenylphosphinpalladium(0) (0.03 mmol), and 0.024 g of triphenylphosphin (0.09 mmol) were dissolved in 20 ml of toluene and stirred for 2 h under reflux. Upon cooling to room temperature, 10 ml of water were added, the aqueous layer was extracted with ethyl acetate, and the combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (10%). Fractions containing the product were combined, the solvent evaporated to yield 0.528 g of the desired product.

후처리

  1. temperatureunder reflux
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washthe combined organic layers were washed with saturated sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. customThe crude product was purified via silica gel chromatography with cyclohexane/ethyl acetate (10%)
  8. additionFractions containing the product
  9. customthe solvent evaporated

출처 및 근거

ORD 기록
ord-b7e49e1d7a8c4bd78b33062ea0e82178
출처 데이터셋
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07851463B2

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