4-Pyridinecarboxaldehyde → 4-(3-Methoxyphenyl)-1-(4-pyridyl)-1-pentene

HRID 261356ノート

反応式

HRID 261356 の反応式
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:10]([CH3:32])[CH2:11][CH2:12][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[CH:8][CH:9]=1.[N:33]1[CH:38]=[CH:37][C:36]([CH:39]=O)=[CH:35][CH:34]=1.[H-].[Na+]>CS(C)=O.O1CCCC1>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:10]([CH3:32])[CH2:11][CH:12]=[CH:39][C:36]2[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=2)[CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 3

HCID 133894-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 204968783-(3-Methoxyphenyl)butyltriphenylphosphonium bromide

生成物 1

HCID 540471774-(3-Methoxyphenyl)-1-(4-pyridyl)-1-pentene

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A mixture of 3-(3-methoxyphenyl)butyl triphenylphosphonium bromide (17.9 g., 35.4 mmoles) in dimethylsulfoxide (50 ml.) is added to 4-pyridinecarboxaldehyde (3.79 g., 35.4 mmoles) in tetrahydrofuran (40 ml.). The resulting mixture is then added dropwise to a slurry of 50% sodium hydride (1.87 g., 39 mmoles) in tetrahydrofuran (20 ml.) under a nitrogen atomosphere at 0°-5° C. Following completion of addition, the mixture is stirred for one hour at 0°-5° and then concentrated under reduced pressure. The concentrate is diluted with water (200 ml.) and then acidified with 6 N HCl. The aqueous acid solution is extracted with benzene (4×50 ml.). It is then made basic and extracted with ethyl acetate (3×50 ml.). Evaporation of the combined extracts after drying (MgSO4) affords 4-(3-methoxyphenyl)-1-(4-pyridyl)-1-pentene as an oil.

後処理

  1. additioncompletion of addition
  2. concentrationconcentrated under reduced pressure
  3. additionThe concentrate is diluted with water (200 ml.)
  4. extractionThe aqueous acid solution is extracted with benzene (4×50 ml.)
  5. extractionextracted with ethyl acetate (3×50 ml.)
  6. customEvaporation of the combined extracts
  7. dry with materialafter drying (MgSO4)

出典と根拠

ORDレコード
ord-562d039506ba413d9ecd58c2ce7e7f1e
出典データセット
uspto-grants-1979_08
特許番号
US04165323

反応ノート

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