Reaktion #52858

Reaktionsgleichung

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

Lösungsmittel

THF

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was quenched by slow addition of cold water
2. 2
   SonstigeSolvent was removed under reduced pressure
3. 3
   Extraktionthe residue was extracted with ethyl acetate
4. 4
   WaschenThe organic layer was washed with brine
5. 5
   Trocknendried (MgSO4) and solvent
6. 6
   Sonstigeremoved under reduced pressure
7. 7
   SonstigeThe crude product was purified by flash chromatography (silica, ethyl acetate/hexane, 1: 3)

Vorschrift

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.

Quelle