Reacción #160758

Ecuación de reacción

NaBH4

5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone

→

5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol

Rendimiento 91.0%

Disolventes

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroquenched
2. 2
   workup.ADDITIONby adding water
3. 3
   Concentraciónconcentrated
4. 4
   Otroto remove the EtOH
5. 5
   workup.ADDITIONadded EtOAc
6. 6
   Extracciónextracted the organics,
7. 7
   Secadodried with brine
8. 8
   ConcentraciónNa2SO4, and concentrated

Procedimiento

To a solution of 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enone (1.0 equiv.) was added EtOH (1.1M) and CeCl3-7H2O (1.3 equiv.). The reaction was cooled to 0° C., then NaBH4 (1.3 equiv.) was added in portions. Stirred for 2 h at 0° C., then quenched by adding water, concentrated to remove the EtOH, added EtOAc, extracted the organics, dried with brine, then Na2SO4, and concentrated to yield 5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enol (91%). LC/MS=235.2 (M+H), LC=2.62 min.

Fuente