반응 #320822

반응 방정식

9-borabicyclo[3.3.1]nonane

3β-(prop-2-enoxy)-17β-(3-furyl)-5β-androstan-14β-ol

sodium hydroxide

hydrogen peroxide

→

3β-(3-hydroxypropoxy)-17β-(3-furyl)-5β-androstan-14β-ol

용매

tetrahydrofuran

tetrahydrofuran

ethanol

반응 조건

후처리

1. 1
   workup.STIRRINGThe mixture was stirred at 50° C. for an hr
2. 2
   기타quenched with a solution of 0.76 g of potassium carbonate in 20 ml of water
3. 3
   workup.DISTILLATIONthe organic solvent distilled under reduced pressure
4. 4
   추출The residue was extracted with methylene chloride
5. 5
   건조the organic solution was dried over anhydrous sodium sulfate
6. 6
   기타evaporated to dryness under reduced pressure
7. 7
   기타The residue was purified by flash-chromatography (SiO2)

실험 절차

To a solution of 0.17 g of 9-borabicyclo[3.3.1]nonane in 35 ml of dry tetrahydrofuran, 0.50 g of 3β-(prop-2-enoxy)-17β-(3-furyl)-5β-androstan-14β-ol in 10 ml of tetrahydrofuran were added under nitrogen atmosphere, at room temperature. The solution was stirred for 6 hrs then 0.75 ml of ethanol, 0.25 ml of sodium hydroxide 6N and 0.50 ml of hydrogen peroxide 30% were added. The mixture was stirred at 50° C. for an hr, quenched with a solution of 0.76 g of potassium carbonate in 20 ml of water and the organic solvent distilled under reduced pressure. The residue was extracted with methylene chloride, the organic solution was dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The residue was purified by flash-chromatography (SiO2) using n-hexane/ethyl acetate 70/30 as eluant to give 0.40 g of 3β-(3-hydroxypropoxy)-17β-(3-furyl)-5β-androstan-14β-ol as a white amorphous solid.

출처