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Dimethyl Sulfoxide → 2-Methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde

HRID 554298
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HRID 554298 반응식
[CH3:1][C:2]1[N:3]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:4]=[CH:5][C:6]=1[CH2:7][OH:8].CS(C)=O.S(=O)(=O)=O.C(=O)([O-])O.[Na+]>C(N(CC)CC)C>[CH3:1][C:2]1[N:3]([S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:11])[CH:4]=[CH:5][C:6]=1[CH:7]=[O:8]
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참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 24682Sulfur trioxideHCID 516892Sodium BicarbonateHCID 66924976[2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol

생성물 1

HCID 862328242-Methyl-1-(phenylsulfonyl)-1H-pyrrole-3-carbaldehyde수율 84%

시약·촉매·용매 1

HCID 8471
Triethylamine
용매

실험 절차

To a mixture of [2-methyl-1-(phenylsulfonyl)-1H-pyrrol-3-yl]methanol (6.35 g), dimethyl sulfoxide (50 mL) and triethylamine (25 mL) was added sulfur trioxide.pyridine complex (4.57 g), and the mixture was stirred at room temperature for 12 hr. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1) to give a white title compound (yield 5.27 g, 84%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogencarbonate solution, water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=2:1)

출처 및 근거

ORD 기록
ord-2cf5c4c266ec4493bc24afb9aa3310e6
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08048909B2

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