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

HRID 2166638Notes

Reaction equation

HRID 2166638 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. 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 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.

Workup

  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)

Sources & evidence

ORD record
ord-843b2f061f834859b6f991f4ce39b3a6
Source dataset
uspto-grants-1983_06
Patent number
US04387229

Reaction notes

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