反应详情

A solution of 0.900 mg of the tosylate 18 in 50 ml of benzene was stirred and purged with N2. Upon addition of 2.3 ml of Vitride reagent (a solution of 70% Na bis(2-methoxyethoxy aluminum hydride in benzene, Aldrich Chemical Co.), the mixture was refluxed (80°) for 18 hours. The product was isolated in the usual manner: after addition of water and 1.0 ml of 10% NaOH, the inorganic precipitate was removed by filtration and washed with ether, the aqueous phase was further extracted with ether, and the combined organic extracts were washed (10% NaOH), and dried over Na2SO4 and evaporated in vacuo. Chromatography of this residue on silica gel (using 20% ethylacetate in Skellysolve B) gave pure 1α-hydroxycholest-5-ene (19), nmr (CDCl3) δ5.53 (1H, m, C-6), 3.74 (1H, m, C-1); mass spectrum, m/e 386 (M+), 371, 368, 273.

1. custompurged with N2
2. additionUpon addition of 2.3 ml of Vitride reagent (a solution of 70% Na bis(2-methoxyethoxy aluminum hydride in benzene, Aldrich Chemical Co.)
3. temperaturethe mixture was refluxed (80°) for 18 hours
4. customThe product was isolated in the usual manner
5. customthe inorganic precipitate was removed by filtration
6. washwashed with ether
7. extractionthe aqueous phase was further extracted with ether
8. washthe combined organic extracts were washed (10% NaOH)
9. dry with materialdried over Na2SO4
10. customevaporated in vacuo