反应详情

A three-necked standard taper round-bottom flask equipped with a mechanical stirrer, dry ice condenser, a nitrogen inlet and an ammonia inlet was thoroughly dried, flushed with nitrogen, cooled in a dry ice-acetone bath and charged with ammonia (60 ml). Lithium (0.4 g, 0.06 mole) was added portionwise under an atmosphere of nitrogen with stirring. A solution of 4,6-cholestadien-1α,3β-diol (4, 0.518 g, 1.29 mmoles) in freshly distilled tetrahydrofuran (60 ml) was added and, after removal of the cooling bath, the reaction mixture was stirred for 3 hours. Ammonium chloride (ca 0.5 g) was added and after stirring for 1 hour, saturated ammonium chloride solution was added. The ammonia was allowed to evaporate. Water was added o the residue and the solution was extracted with ether. The combined organic extracts were washed with water, dried over anhydrous sodium sulfate, filtered and the filtrate was evaporated under vacuum. Filtration of the residual solid (0.509 g) dissolved in low boiling petroleum ether through a column of silica gel gave 0.3 g (60%) of carbinol 5.

1. customA three-necked standard taper round-bottom flask equipped with a mechanical stirrer, dry ice condenser, a nitrogen inlet and an ammonia inlet
2. customwas thoroughly dried
3. customflushed with nitrogen
4. temperaturecooled in a dry ice-acetone bath
5. additioncharged with ammonia (60 ml)
6. customafter removal of the cooling bath
7. stirringthe reaction mixture was stirred for 3 hours
8. additionAmmonium chloride (ca 0.5 g) was added
9. stirringafter stirring for 1 hour
10. additionsaturated ammonium chloride solution was added
11. customto evaporate
12. additionWater was added o the residue
13. extractionthe solution was extracted with ether
14. washThe combined organic extracts were washed with water
15. dry with materialdried over anhydrous sodium sulfate
16. filtrationfiltered
17. customthe filtrate was evaporated under vacuum
18. filtrationFiltration of the residual solid (0.509 g)
19. dissolutiondissolved