Water → 4-(2-(4-Formylphenyl)ethenyl)pyridine

HRID 636515노트

반응식

HRID 636515 반응식
[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:16]=[CH:15][C:12]([CH2:13][OH:14])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.C(N(CC)CC)C.O>CS(C)=O>[N:1]1[CH:6]=[CH:5][C:4](/[CH:7]=[CH:8]/[C:9]2[CH:10]=[CH:11][C:12]([CH:13]=[O:14])=[CH:15][CH:16]=2)=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 8471TriethylamineHCID 70240750(4-(2-(Pyridin-4-YL)vinyl)phenyl)methanol

생성물 1

HCID 53747304-(2-(4-Formylphenyl)ethenyl)pyridine수율 70.7%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

To a solution of 4-[(E)-2-(4-pyridyl)vinyl]benzyl alcohol (740 mg) and triethylamine (1.77 g) in dimethyl sulfoxide (3 ml) was added sulfur trioxide—pyridine complex (1.11 g) at ambient temperature, and after stirring for 4 hours, water was added thereto. The mixture was extracted with ethyl acetate, and the extract was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (chloroform—ethyl acetate) and crystallized with diisopropyl ether to give 4-[(E)-2-(4-pyridyl)vinyl]-benzaldehyde (518 mg).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (chloroform—ethyl acetate)
  6. customcrystallized with diisopropyl ether

출처 및 근거

ORD 기록
ord-e8e367e5e80e49d28f1041d9804717ab
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194396B1

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