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Water → 2-Ethenyl-5-nitropyridine

HRID 1260219
ノート
印刷プレビュー

反応式

HRID 1260219 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

HCID 230905502-Ethenyl-5-nitropyridine収率 111.6%

試薬・触媒・溶媒 2

HCID 11776Triphenylphosphine触媒HCID 1140Toluene溶媒

実験手順

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 agueous 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.

後処理

  1. temperatureunder reflux
  2. extractionthe agueous 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

出典と根拠

ORDレコード
ord-cbba961876e6489b8fb60fe47d0e55ed
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08470810B2

反応ノート

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