Réaction #2028903

Équation de réaction

THF

4-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-carboaldehyde

THF

methoxymethyltriphenylphosphonium chloride

Potassium t-butoxide

→

4-ethoxy-2,2′,3,3′-tetrafluoro-4′-(2-methoxyvinyl)biphenyl

Rendement 94.5%

Solvants

water

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.WAITthe stirring was continued for 1 hour
3. 3
   TempératureThe reaction mixture was warmed to room temperature
4. 4
   Autreto give two layers
5. 5
   ExtractionThe water layer was extracted with toluene (100 ml) three times
6. 6
   Lavagethe combined organic layer was washed with water
7. 7
   Séchagedried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
9. 9
   AutreThe residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene)

Mode opératoire

THF (150 ml) was added to methoxymethyltriphenylphosphonium chloride (26.8 g) in a reaction vessel under an atmosphere of nitrogen and the solution was cooled to −20° C. Potassium t-butoxide (10.1 g) was added, and the stirring was continued for 1 hour. A THF (100 ml) solution of 4-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-carboaldehyde (7) (17.9 g) prepared in the fifth step was added dropwise, and the stirring was continued for 1 hour. The reaction mixture was warmed to room temperature and water (200 ml) was added to give two layers. The water layer was extracted with toluene (100 ml) three times, and the combined organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene) to give 4-ethoxy-2,2′,3,3′-tetrafluoro-4′-(2-methoxyvinyl)biphenyl (8) (18.5 g) in 94.5% yield.

Source