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

HRID 26088

반응식

HRID 26088 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매2회

실험 절차

A mixture of 3-(3-methoxyphenyl)butyl triphenylphosphonium bromide (17.5 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 atmosphere at 0°-5° C. Following completion of addition, the mixture is stirred for one hour at 0°-5° C. and then concentrated under reduced pressure. The concentrate is diluted with water (200 ml.) and then acidified with 6N 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-82dad07c0bb24612af1f92dd1c4e46fd
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147872

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