反应详情

温度

0 °C

The product of Example 1B (931 mg, 3.33 mmole) and osmium tetraoxide (28 mg, cat.) were dissolved in 30 ml THF and 15 ml water. The solution was cooled to 0° C. Sodium periodate (1.5 g, 7.0 mmole) was added in small portions. The mixture was stirred at room temperature overnight. The solution was quenched with water, and extracted three times with dichloromethane. The combined organics were dried over sodium sulfate and concentrated to give the crude product, which was purified by chromatography (20% hexane in dichloromethane) to give the title compound (710 mg, 76%). 1H NMR (500 MHz, CDCl3) δ ppm 8.00 (d, J=1.87 Hz, 1H), 7.84 (d, J=8.74 Hz, 1H), 7.59 (dd, J=8.73, 1.87 Hz, 1H), 3.96-4.10 (m, 1H), 3.54-3.76 (m, 4H). MS: (M+H)+=281/283

1. customThe solution was quenched with water
2. extractionextracted three times with dichloromethane
3. dry with materialThe combined organics were dried over sodium sulfate
4. concentrationconcentrated
5. customto give the crude product, which
6. customwas purified by chromatography (20% hexane in dichloromethane)