反応 #58885

反応方程式

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

hydrochloric acid

1,3-Bis(diphenylphosphino)propane

potassium carbonate

Butoxy-ethene

→

title product

収率 42.0%

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

収率 42.0%

溶媒

DMF

H2O

反応条件

後処理

1. 1
   抽出extracted with CH2Cl2
2. 2
   その他The organic phase was evaporated on celite
3. 3
   その他the residue was purified by flash chromatography

実験手順

(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).

出典