Water → methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate

HRID 636513

反応式

HRID 636513 の反応式
[OH-].[Na+].[Br-].[CH3:4][O:5][C:6]([C:8]1[CH:33]=[CH:32][C:11]([CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:10][CH:9]=1)=[O:7].[N:34]1[CH:39]=[CH:38][C:37]([CH:40]=O)=[CH:36][CH:35]=1.O>CS(C)=O>[N:34]1[CH:39]=[CH:38][C:37](/[CH:40]=[CH:12]/[C:11]2[CH:10]=[CH:9][C:8]([C:6]([O:5][CH3:4])=[O:7])=[CH:33][CH:32]=2)=[CH:36][CH:35]=1.[N:34]1[CH:39]=[CH:38][C:37](/[CH:40]=[CH:12]\[C:11]2[CH:10]=[CH:9][C:8]([C:6]([O:5][CH3:4])=[O:7])=[CH:33][CH:32]=2)=[CH:36][CH:35]=1

参加物

7

反応物 4

HCID 962WaterHCID 133894-PyridinecarboxaldehydeHCID 14798Sodium HydroxideHCID 2764257[4-(Methoxycarbonyl)benzyl](triphenyl)phosphonium bromide

生成物 2

HCID 12006312methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoateHCID 70244616methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a solution of sodium hydroxide (830 mg) in dimethylsulfoxide (100 ml) was added (4-methoxycarbonylbenzyl)triphenylphosphonium bromide (10.0 g), and after 30 minutes, 4-pyridinecarbaldehyde (2.22 g) was added thereto under ice-cooling. The mixture was stirred overnight. Water was added to the reaction mixture, and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (n-hexane—ethyl acetate) to give methyl 4-[(E)-2-(4-pyridyl)vinyl]benzoate (1.18 g) and methyl 4-[(Z)-2-(4-pyridyl)vinyl]benzoate (2.67 g).

後処理

  1. temperatureunder ice-cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (n-hexane—ethyl acetate)

出典と根拠

ORDレコード
ord-61dcf52438ce4715b2d32a7ba6886700
出典データセット
uspto-grants-2001_02
特許番号
US06194396B1

関連ノート

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