Reaktion #1765751

Reaktionsgleichung

2-(4-bromophenoxy)-2,3-dihydro-1H-indene

sodium hydrogen carbonate

methyl acrylate

→

title compound

Ausbeute 69.4%

Methyl (E)-3-[4-[(2,3-dihydro-1H-inden-2-yl)oxy]phenyl]-2-propenoate

Ausbeute 69.4%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas returned to room temperature
2. 2
   Filtrationfiltered
3. 3
   workup.ADDITIONWater was added
4. 4
   Extraktionthe reaction mixture was extracted with ethyl acetate
5. 5
   WaschenThe extract was washed with saturated brine
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was recrystallized from ethyl acetate-hexane

Vorschrift

To a solution of 2-(4-bromophenoxy)-2,3-dihydro-1H-indene (1.4 g, 4.7 mmol) in N,N-dimethylformamide (4.7 mL) were added sodium hydrogen carbonate (1.0 g, 12 mmol), methyl acrylate (0.86 mL, 9.5 mmol), tetrabutylammonium chloride (2.0 g, 7.1 mmol) and palladium acetate (31 mg, 0.14 mmol), and the mixture was stirred at 100° C. for 24 hours. The reaction solution was returned to room temperature, and then filtered. Water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with saturated brine, then dried over anhydrous magnesium sulfate and concentrated. The residue was recrystallized from ethyl acetate-hexane to give the title compound (0.96 g, yield 69%).

Quelle