Reacción #164824

Ecuación de reacción

1,7-Diphenyl-1,6-heptadiene-3,5-dione

→

orange-yellow oil

Rendimiento 71.3%

1,7-Diphenylheptane-3,5-dione

Rendimiento 71.3%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofor 4 hr
2. 2
   Otroat room temperature
3. 3
   FiltraciónThe resulting mixture was filtered through celite
4. 4
   Otrothe solvent evaporated
5. 5
   Otroto afford an oil
6. 6
   OtroThe crude oil was purified by preparative thin layer chromatography with ethyl acetate/hexane

Procedimiento

1,7-Diphenyl-1,6-heptadiene-3,5-dione (3b, 0.56 g, 2.0 mmol) and palladium on activated carbon (0.25 g, 5%) were combined in ethyl acetate (40 ml). The mixture was placed under a hydrogen atmosphere (60 psi) on a Parr apparatus for 4 hr at room temperature. The resulting mixture was filtered through celite and the solvent evaporated to afford an oil. The crude oil was purified by preparative thin layer chromatography with ethyl acetate/hexane to give 0.40 g (70%) of an orange-yellow oil; 1H NMR: δ enol form: 2.53 (m, 4H), 2.83 (m, 4H), 5.47 (s, 1H), 7.30 (m, 10H); keto form: 2.53 (m, 4H), 2.83 (m, 4H), 3.54 (s, 2H), 7.30 (m, 10H); 13C NMR: δ 29.4, 31.5, 39.9, 45.0, 99.5, 126.1, 128.3, 128.5, 140.5, 170.4, 172.0, 192.8.

Fuente