反应详情

2,6-Dimethylpyridine (6.1 mL, 52.9 mmol, 2.0 equiv), osmium tetroxide (2.5% w/v solution in tert-butyl alcohol, 6.6 mL, 0.53 mmol, 0.02 equiv), and sodium periodate (23.1 g, 106 mmol 4.0 equiv) were added sequentially to a solution of ethyl 2-methyl-2-(methylsulfonyl)hex-5-enoate (6.2 g, 26.0 mmol, 1.0 equiv) in 1,4-dioxane-water (3:1, 0.27 L) at room temperature. After vigorously stirring overnight (approx. 18 h), the reaction was partitioned between dichloromethane (0.2 L) and water (0.2 L). The aqueous phase was extracted with dichloromethane (0.2 L). The combined organic phases were washed with brine (30 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide the title compound as an oil (6.2 g). MS (GCMS) m/z 237 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ1.34 (t, J=7.22 Hz, 3H) 1.63 (s, 3H) 2.21-2.39 (m, 1H) 2.56 (s, 2H) 2.65-2.81 (m, 1H) 3.05-3.17 (m, 3H) 4.30 (q, J=7.15 Hz, 2H) 9.79 (s, 1H).

1. customthe reaction was partitioned between dichloromethane (0.2 L) and water (0.2 L)
2. extractionThe aqueous phase was extracted with dichloromethane (0.2 L)
3. washThe combined organic phases were washed with brine (30 mL)
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure