반응 #52858

반응 방정식

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

용매

THF

EtOH

반응 조건

후처리

1. 1
   기타The reaction was quenched by slow addition of cold water
2. 2
   기타Solvent was removed under reduced pressure
3. 3
   추출the residue was extracted with ethyl acetate
4. 4
   세척The organic layer was washed with brine
5. 5
   건조dried (MgSO4) and solvent
6. 6
   기타removed under reduced pressure
7. 7
   기타The crude product was purified by flash chromatography (silica, ethyl acetate/hexane, 1: 3)

실험 절차

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.

출처