반응 #320821

반응 방정식

allyl bromide

17β-(3-furyl)-5β-androstane-3β,14β-diol

sodium hydride

→

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

수율 87.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도at reflux temperature for 6 hrs
2. 2
   기타The mixture was quenched with water
3. 3
   workup.DISTILLATIONthe organic solvent was distilled under reduced pressure
4. 4
   추출The residue was extracted with ethyl acetate
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 0.60 g of 17β-(3-furyl)-5β-androstane-3β,14β-diol (II-a: Ref. comp.) (Minato H. and Nagasaki T., J. Chem. Soc.(C), 1966, 377) in 50 ml of dry tetrahydrofuran, 0.44 g of sodium hydride (60% dispersion in mineral oil) were added under nitrogen atmosphere at room temperature and the resulting mixture was stirred at reflux temperature for 6 hrs; 1.4 g of allyl bromide were added and the reflux continued for further 20 hrs. The mixture was quenched with water and the organic solvent was distilled under reduced pressure. The residue was extracted with ethyl acetate, 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 80/20 as eluant to give 0.58 g of 3β-(prop-2-enoxy)-17β-(3-furyl)-5β-androstan-14β-ol as a white solid.

출처