反应详情

To a solution of (COCl)2 (3.4 ml) in CH2Cl2 (100 ml) was dropwise added DMSO (3.7 ml) at −78° C. After 10minutes, a solution of (1R,2R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1,2-dihydroxycyclohexane (12 g) in CH2Cl2(50 ml) was added to the above mixture at the same temperature. After 10 minutes, the mixture was added with triethylamine (15 ml) and allowed to stand at room temperature. After evaporating the solvent, the residue was partitioned between EtOAc and water. The organic layer was washed with water and brine. The organic solvent was evaporated in vacuo to give an oily compound. The oily compound was dissolved in DMF (50 ml) and then added with trimethylsilychloride (6.6 ml) and imidazole(7.0 g) at room temperature. After stirring for 5 hours, the mixture was partitioned between EtOAc and water. The organic solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel to give (R)-1-[3-(tertbutyldiphenylsilyloxy)benzyl]-1-trimethylsilyoxy-2-cyclohexanone (1.15 g).

1. customat −78° C
2. waitAfter 10 minutes
3. customto stand at room temperature
4. customAfter evaporating the solvent
5. customthe residue was partitioned between EtOAc and water
6. washThe organic layer was washed with water and brine
7. customThe organic solvent was evaporated in vacuo
8. customto give an oily compound
9. customthe mixture was partitioned between EtOAc and water
10. customThe organic solvent was evaporated in vacuo
11. customThe residue was purified by chromatography on silica gel