تفاعل #948990

معادلة التفاعل

hydrogen peroxide

3-benzoyloxy-4,4-dimethylcholesta-8,14-diene

borane

sodium hydroxide

→

3-benzoyloxy-4,4-dimethylcholest-8-en-15-ol

المذيبات

diethyl ether

water

THF

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled to 0° C.
2. 2
   workup.ADDITIONwas added to the mixture
3. 3
   استخلاصthe aqueous phase extracted twice with diethyl ether
4. 4
   غسيلThe combined organic phases were washed twice with sodium bisulphite solution
5. 5
   أخرىAfter evaporation
6. 6
   أخرىthe product was purified by chromatography on SiO2 (2% diethyl ether in toluene)

الإجراء التجريبي

2.04 g of 3-benzoyloxy-4,4-dimethylcholesta-8,14-diene (Step A) was dissolved in 50 ml of THF, and 360 ml of 1M borane in THF was added dropwise at 0° C. The mixture was stirred at ambient temperature overnight, cooled to 0° C., and 140 ml of water was added dropwise, followed by 360 ml of 10% sodium hydroxide and 378 ml of 30% hydrogen peroxide. After stirring for 90 mutes, 100 ml of diethyl ether was added to the mixture and the aqueous phase extracted twice with diethyl ether. The combined organic phases were washed twice with sodium bisulphite solution and then with water. After evaporation, the product was purified by chromatography on SiO2 (2% diethyl ether in toluene) to yield 0.62 g of 3-benzoyloxy-4,4-dimethylcholest-8-en-15-ol.

المصدر