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

HRID 636515ノート

反応式

HRID 636515 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 53747304-(2-(4-Formylphenyl)ethenyl)pyridine収率 70.7%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e8e367e5e80e49d28f1041d9804717ab
出典データセット
uspto-grants-2001_02
特許番号
US06194396B1

反応ノート

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