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

HRID 1074501Notes

Reaction equation

HRID 1074501 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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. 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 benzene (3×50 ml.). Evaporation of the combined extracts after drying (MgSO4) affords 4-(3-methoxyphenyl)-1-(4-pyridyl)-1-pentene as an oil.

Workup

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

Sources & evidence

ORD record
ord-d1f1a8de67aa43118f1a0055f5f10a0f
Source dataset
uspto-grants-1983_07
Patent number
US04391827

Reaction notes

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