Reacción #944017

Ecuación de reacción

hydrochloric acid

triethylamine

β-piperidinostyrene diethyl phthalate

4-fluorophenacyl bromide

→

title compound

Rendimiento 17.1%

3-(4-Fluorobenzoyl)-2-phenylpropionaldehyde

Rendimiento 17.1%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature for a further 1 hour
2. 2
   ExtracciónIt was then extracted with diethyl ether
3. 3
   ExtracciónThe organic extract
4. 4
   Lavadowas washed with water
5. 5
   Secadodried over anhydrous sodium sulfate
6. 6
   OtroThe solvent was then removed by distillation under reduced pressure
7. 7
   Lavadoeluted with a 95:5 by volume mixture of hexane and ethyl acetate

Procedimiento

4.68 g of the β-piperidinostyrene/diethyl phthalate mixture were dissolved in 70 ml of anhydrous tetrahydrofuran, and 1.01 g (10 mmol) of triethylamine were added to the resulting solution. 2.60 g (12 mmol) of 4-fluorophenacyl bromide were then added to the resulting mixture, which was then stirred at room temperature for 3 hours. At the end of this time, 30 ml of 1N aqueous hydrochloric acid were added to the reaction mixture, and the mixture was stirred at room temperature for a further 1 hour. It was then extracted with diethyl ether. The organic extract was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure and the residue was applied to a silica gel chromatography column and eluted with a 95:5 by volume mixture of hexane and ethyl acetate, to give 0.50 g of the title compound as a slightly yellow oily substance.

Fuente