تفاعل #52858

معادلة التفاعل

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

المذيبات

THF

EtOH

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched by slow addition of cold water
2. 2
   أخرىSolvent was removed under reduced pressure
3. 3
   استخلاصthe residue was extracted with ethyl acetate
4. 4
   غسيلThe organic layer was washed with brine
5. 5
   تجفيفdried (MgSO4) and solvent
6. 6
   أخرىremoved under reduced pressure
7. 7
   أخرىThe crude product was purified by flash chromatography (silica, ethyl acetate/hexane, 1: 3)

الإجراء التجريبي

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.

المصدر