Reaktion #95080

Reaktionsgleichung

triphenyl(1[ethoxycarbonyl]ethylidene)phosphorane

3-nitrobenzaldehyde

→

title product

Ethyl 2-Methyl-3-(3-Nitrophenyl)propenoate

Lösungsmittel

benzene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux overnight
2. 2
   TemperaturThe reaction mixture was cooled
3. 3
   Sonstigethe solvent was removed by evaporation in vacuo
4. 4
   ExtraktionThe residue was extracted with 300 ml
5. 5
   FiltrationThe isopropyl ether solution was filtered
6. 6
   Sonstigethe filtrate was evaporated in vacuo
7. 7
   workup.DISTILLATIONThe residue was distilled under reduced pressure
8. 8
   Sonstigegiving 37.6 g

Vorschrift

To a stirred slurry of 79.8 g. of triphenyl(1[ethoxycarbonyl]ethylidene)phosphorane in 300 ml. of benzene was added 30.2 g. of 3-nitrobenzaldehyde and the resulting mixture was heated under reflux overnight. The reaction mixture was cooled and the solvent was removed by evaporation in vacuo. The residue was extracted with 300 ml. of isopropyl ether. The isopropyl ether solution was filtered, and the filtrate was evaporated in vacuo. The residue was distilled under reduced pressure, giving 37.6 g. of the title product, b.p. 147°-162° C./0.25 mm Hg. The NMR spectrum (in CDCl3) showed absorptions at 1.4 (t), 2.1 (d), 4.3 (q), 7.4 (m) and 8.1 (m) ppm.

Quelle