Reaktion #58885

Reaktionsgleichung

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

hydrochloric acid

1,3-Bis(diphenylphosphino)propane

potassium carbonate

Butoxy-ethene

→

title product

Ausbeute 42.0%

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

Ausbeute 42.0%

Lösungsmittel

DMF

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with CH2Cl2
2. 2
   SonstigeThe organic phase was evaporated on celite
3. 3
   Sonstigethe residue was purified by flash chromatography

Vorschrift

(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).

Quelle