Reaktion #54366

Reaktionsgleichung

3-(3-methoxyphenyl)butyl triphenylphosphonium bromide

sodium hydride

4-pyridinecarboxaldehyde

→

4-(3-methoxyphenyl)-1-(4-pyridyl)-1-pentene

Lösungsmittel

dimethylsulfoxide

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONcompletion of addition
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   workup.ADDITIONThe concentrate is diluted with water (200 ml.)
4. 4
   ExtraktionThe aqueous acid solution is extracted with benzene (4 × 50 ml.)
5. 5
   Extraktionextracted with ethyl acetate (3 × 50 ml.)
6. 6
   SonstigeEvaporation of the combined extracts
7. 7
   Trocknenafter drying (MgSO4)

Vorschrift

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.

Quelle