Reacción #52858

Ecuación de reacción

ethyl 4-[(5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-yl)azo]benzoate

NaBH4

→

title compound

(+/−) Ethyl 4-[(5,5-dimethyl-8-hydroxy-5,6,7,8-tetrahydronaphthalen-2-yl)azo]benzoate

Disolventes

THF

EtOH

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction was quenched by slow addition of cold water
2. 2
   OtroSolvent was removed under reduced pressure
3. 3
   Extracciónthe residue was extracted with ethyl acetate
4. 4
   LavadoThe organic layer was washed with brine
5. 5
   Secadodried (MgSO4) and solvent
6. 6
   Otroremoved under reduced pressure
7. 7
   OtroThe crude product was purified by flash chromatography (silica, ethyl acetate/hexane, 1: 3)

Procedimiento

To a solution of ethyl 4-[(5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-yl)azo]benzoate (Compound D10, 60 mg, 0.171 mmol) in 2 ml of THF and 7 ml of EtOH at 0 IC was added NaBH4 (6.5 mg, 0.171 mmol) and the mixture stirred for 3 h. The reaction was quenched by slow addition of cold water. Solvent was removed under reduced pressure and the residue was extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and solvent removed under reduced pressure. The crude product was purified by flash chromatography (silica, ethyl acetate/hexane, 1: 3) to afford the title compound as a red oil.

Fuente