Reaktion #1909465

Reaktionsgleichung

HCl

3-benzyloxy-5-methyl-phenol

3-(4-fluoro-2-methyl-phenyl)-acrylic acid ethyl ester

potassium carbonate

→

title compound

Ausbeute 58.6%

3-[4-(3-Benzyloxy-5-methyl-phenoxy)-2-methyl-phenyl]-acrylic acid ethyl ester

Ausbeute 58.6%

Lösungsmittel

Et2O

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction is cooled
2. 2
   Extraktionextracted with water
3. 3
   TrocknenThe organic layer is dried (Na2SO4)
4. 4
   Sonstigethe solvent is removed in vacuo
5. 5
   Sonstigeto afford crude product that
6. 6
   Sonstigeis absorbed on silica gel
7. 7
   Sonstigepurified by flash chromatography

Vorschrift

A mixture of 3-benzyloxy-5-methyl-phenol (3.24 g, 15.1 mmol), 3-(4-fluoro-2-methyl-phenyl)-acrylic acid ethyl ester (3.15 g, 15.1 mmol) and 325 mesh potassium carbonate (2.51 g, 18.2 mmol) in dry DMSO (40 mL) is heated to 130° C. and stirred for 20 hours under N2. The reaction is cooled and acidified with 1 N HCl (30 mL). The mixture is then diluted with Et2O and extracted with water. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/ethyl acetate to afford 3.56 g (58%) of the title compound. Rf=0.39 (4/1 hexanes/EtOAc). 1H NMR (400 MHz, CDCl3); MS (ES+) m/z mass calculated for C26H26O4 402, found 403 (M+1, 100%).

Quelle