反应详情

1-Allyl-cyclohexane-1,4-dicarboxylic acid dimethyl ester (4.5 g, 17.71 mmol) was dissolved in 2-propanol (100 mL) and water (50 mL). To this was added an aqueous solution of NaIO4 (9.5 g, 44.3 mmol) in water (50 mL), followed by addition of OsO4 (0.025 g, crystals, in one portion). The reaction mixture was allowed to stir for 16 hours. Then, the reaction mixture was poured into ice water (50 mL) and ethyl acetate (EtOAc) (60 mL). The two layers were separated and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic solutions were washed with brine, and concentrated to dryness. The material was then purified over silica gel column eluting with ethyl acetate in heptanes (0-60%) to afford 3.09 g (72%) of the title compound.

1. customThe two layers were separated
2. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
3. washThe combined organic solutions were washed with brine
4. concentrationconcentrated to dryness
5. customThe material was then purified over silica gel column
6. washeluting with ethyl acetate in heptanes (0-60%)