Reaktion #165208

Reaktionsgleichung

Sodium hydride

Furfural

ethyl 4-bromomethylbenzoate

triethylphosphite

→

title compound

Ausbeute 42.0%

4-((E)-2-furan-2-yl-vinyl)-benzoic acid ethyl ester

Ausbeute 42.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   workup.STIRRINGstirred for 2 hours at room temperature
3. 3
   SonstigeThe reaction mixture was partitioned into water and ethyl acetate on an ice bath (0° C.)
4. 4
   WaschenThe organic layer was washed with water and saturated aqueous sodium chloride
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated under a reduced pressure
7. 7
   SonstigeThe residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:20)

Vorschrift

60% Sodium hydride (0.48 g, 12 mmol) was suspended in anhydrous tetrahydrofuran (10 mL) under nitrogen atmosphere, and diethyl 4-ethoxycarbonyl benzylphosphonate (3.6 g, 12 mmol) prepared from ethyl 4-bromomethylbenzoate and triethylphosphite according to the methods as similar to those of Manufacturing Example 93-1-1 was added at room temperature and stirred for 30 minutes at room temperature. Furfural (1 g, 10.4 mmol) was then added at room temperature, and stirred for 2 hours at room temperature. The reaction mixture was partitioned into water and ethyl acetate on an ice bath (0° C.). The organic layer was washed with water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by NH silica gel column chromatography (ethyl acetate:heptane=1:20) to obtain the title compound (1.07 g, 42%).

Quelle