4-Pyridinecarboxaldehyde → HCID 54288490, compound

HRID 435134Notes

Reaction equation

HRID 435134 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH:12]([CH3:34])[CH2:13][CH2:14][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1.[N:35]1[CH:40]=[CH:39][C:38]([CH:41]=O)=[CH:37][CH:36]=1.[H-].[Na+]>CS(C)=O.O1CCCC1>[CH3:11][O:10][C:8]1[CH:7]=[C:6]([CH:12]([CH3:34])[CH2:13][CH:14]=[CH:41][C:38]2[CH:39]=[CH:40][N:35]=[CH:36][CH:37]=2)[CH:5]=[C:4]([O:3][CH3:2])[CH:9]=1

Participants

6

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 24758Sodium hydrideHCID 20487382HCID 20487382, compound

Product 1

HCID 54288490HCID 54288490, compoundYield 70.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 3-(3,5-dimethoxyphenyl)butyl triphenylphosphonium bromide (19.0 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-(3,5-dimethoxyphenyl)-1-(4-pyridyl)-1-pentene (7.1 g., 70%) 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-3fe326a02d3444688dcbe176247f611d
Source dataset
uspto-grants-1983_08
Patent number
US04400385

Reaction notes

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