Reacción #160752

Ecuación de reacción

5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone

NaBH4

→

5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

Rendimiento 74.0%

Disolventes

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched by 5 mL of water
2. 2
   OtroThe volatiles were removed in vacuum
3. 3
   Otrothe residue was partitioned between EtOAc and H2O
4. 4
   OtroThe organic layer was separated
5. 5
   Lavadowashed with brine
6. 6
   ExtracciónThe combined aqueous was back extracted with EtOAc
7. 7
   Lavadothe organic was washed with brine
8. 8
   SecadoThe combined organics were dried over MgSO4
9. 9
   Filtraciónfiltered
10. 10
    Concentraciónconcentrated
11. 11
    OtroThe residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes)

Procedimiento

To a solution of 5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1.0 eq), and CeCl3-7H2O (1.2 eq) in MeOH (0.2 M) was added NaBH4 (1.0 eq) at 0° C. The solution was stirred for 1 hour, and then quenched by 5 mL of water. The volatiles were removed in vacuum and the residue was partitioned between EtOAc and H2O. The organic layer was separated and washed with brine. The combined aqueous was back extracted with EtOAc and the organic was washed with brine. The combined organics were dried over MgSO4, filtered and concentrated. The residue was purified by column (5% methanol in 1:1 ethyl acetate and hexanes) to give 5,5-dimethyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (74%). LC/MS (m/z): MH+=249.2, Rt=0.76 min.

Fuente