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

HRID 636513

반응식

HRID 636513 반응식
[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

참가 물질

7

반응물 4

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

생성물 2

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

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-61dcf52438ce4715b2d32a7ba6886700
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194396B1

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