Reaktion #42156

Reaktionsgleichung

4′-chloroacetophenone

styrene

dicyclohexylmethylamine

→

(trans)-4-acetylstilbene

Ausbeute 75.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 30-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   SonstigeThe flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 30° C. for 37 hours
5. 5
   SonstigeAfter the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution
6. 6
   workup.ADDITIONwere added
7. 7
   Sonstigefollowed by separation
8. 8
   SonstigeThe organic phase was purified by column chromatography

Vorschrift

A 30-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.773 g (5 mmol) of 4′-chloroacetophenone, 1.042 g (10 mmol) of styrene, 0.034 g (0.038 mmol) of tris(dibenzylideneacetone)dipalladium (0), 1.074 g (5.5 mmol) of dicyclohexylmethylamine and 5 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.078 g (0.15 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 30° C. for 37 hours. After the completion of the reaction, 5 ml of toluene and 10 ml of saturated sodium chloride solution were added, followed by separation. The organic phase was purified by column chromatography to afford 0.834 g of (trans)-4-acetylstilbene (yield: 75 mol % based on 4′-chloroacetophenone). The identification of the product was made by mass spectroscopy, 1H-NMR and 13C-NMR.

Quelle