Reaktion #796790

Reaktionsgleichung

Water

ethyl diethylphosphonoacetate

sodium hydride

cyclopropyl(6-methoxypyrimidin-4-yl)methanone

→

title compound

ethyl 3-cyclopropyl-3-(6-methoxypyrimidin-4-yl)acrylate

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeobtained in Example 2, step C
2. 2
   Extraktionthe mixture was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed with water and saturated brine
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   Sonstigethe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
7. 7
   Sonstigeto give

Vorschrift

Under a nitrogen atmosphere, to a suspension of 60% sodium hydride (2.13 g) in THF (100 ml) was added ethyl diethylphosphonoacetate (13.2 mL) at 0° C. To the obtained solution was added cyclopropyl(6-methoxypyrimidin-4-yl)methanone (entire amount) obtained in Example 2, step C, and the mixture was stirred at 0° C. for 1 hr. Water was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give an isomer mixture of the title compound (E:Z=93:7 or 7:93, 5.57 g) as a yellow oil.

Quelle