Reacción #58885

Ecuación de reacción

(5-Bromo-2-methoxy-benzyl)-dimethyl-amine

hydrochloric acid

1,3-Bis(diphenylphosphino)propane

potassium carbonate

Butoxy-ethene

→

title product

Rendimiento 42.0%

1-(3-Dimethylaminomethyl-4-methoxy-phenyl)-ethanone

Rendimiento 42.0%

Disolventes

DMF

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with CH2Cl2
2. 2
   OtroThe organic phase was evaporated on celite
3. 3
   Otrothe residue was purified by flash chromatography

Procedimiento

(5-Bromo-2-methoxy-benzyl)-dimethyl-amine (29 mmol), Butoxy-ethene (100 mmol), Palladium acetate (0.9 mmol), 1,3-Bis(diphenylphosphino)propane (1.8 mmol), and potassium carbonate were suspended in DMF (50 ml) and H2O under argon. Heated at 80° C. overnight. Poured into hydrochloric acid (2 M) and stirred for 1 hour. The mixture was adjusted to basic pH and extracted with CH2Cl2. The organic phase was evaporated on celite and the residue was purified by flash chromatography to give the title product as orange oil in 42% yield. 1H-NMR (CDCl3) δ 7.90 (s, 1H), 7.88 (dd, 1H), 6.89 (d, 1H), 3.88 (s, 3H), 3.44 (s, 2H), 2.55 (s, 3H), 2.25 (s, 6H).

Fuente