Reacción #321434

Ecuación de reacción

sodium hydroxide

2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-5-nitro-2,3-dihydrobenzofuran

→

desired compound

Rendimiento 61.6%

5-Amino-2,2,4,6,7-pentamethyl-3-(4-methylphenyl)-2,3-dihydrobenzofuran

Rendimiento 61.6%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was heated
2. 2
   Temperaturaunder reflux for 3 hours
3. 3
   FiltraciónInsoluble materials were filtered off
4. 4
   workup.ADDITIONwater was added
5. 5
   ExtracciónThe mixture was extracted with ethyl acetate
6. 6
   LavadoThe extract was washed with water
7. 7
   Otrodried
8. 8
   workup.DISTILLATIONthe solvent was distilled off
9. 9
   OtroThe residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 95:5)
10. 10
    Otrocrystallized from hexane

Procedimiento

2,2,4,6,7-Pentamethyl-3-(4-methylphenyl)-5-nitro-2,3-dihydrobenzofuran (1.26 g, 3.9 mmol) was dissolved in methanol (30 ml). Zinc powder (1.3 g) and 1N sodium hydroxide (15 ml) were added to the solution and the mixture was heated under reflux for 3 hours. Insoluble materials were filtered off and water was added. The mixture was extracted with ethyl acetate. The extract was washed with water, dried and then the solvent was distilled off. The residue was purified by column chromatography on silica gel (hexane-isopropyl ether, 95:5) and crystallized from hexane to obtain the desired compound (710 mg, yield: 53.7%), m.p. 119°-120° C.

Fuente