反应详情

A solution of 24 mg (0.08 mMol) of (4aR,5R,8aR)-5-[(R)-5-Hydroxy-1,5-dimethyl-hexyl]-4a-methyl-octahydro-naphtalen-1-one in 0.5 ml of tetrahydrofuran is cooled under stirring and Argon atmosphere to 0°. The reaction mixture is stirred for an additional hour after addition of 12 μl (0.08 mMol) of trimethylsilylimidazole, of 5.1 μl (0.04 mMol) of trimethylsilylchloride and of 2.8 mg (0.04 mMol) of imidazole. The reaction mixture is poured into ice water, extracted three times with diethylether, the combined organic extracts are washed twice with brine and dried over Na2SO4. The organic solvent is evaporated in vacuo and the residue is chromatographed over 5 g of silicagel with hexane/diethylether 9/1 to yield 25 mg of pure, oily (4aR,5R,8aR)-5-[(R)-1,5-Dimethyl-5-trimethylsilanyloxy-hexyl]-4a-methyl -octahydro-naphtalen-1-one

1. customto 0°
2. stirringThe reaction mixture is stirred for an additional hour
3. extractionextracted three times with diethylether
4. washthe combined organic extracts are washed twice with brine
5. dry with materialdried over Na2SO4
6. customThe organic solvent is evaporated in vacuo
7. customthe residue is chromatographed over 5 g of silicagel with hexane/diethylether 9/1