反応 #2028903

反応方程式

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

収率 94.5%

溶媒

water

反応条件

後処理

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

実験手順

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.

出典