反应详情

Sodium hydroxide (1.89 g, 16 mmol) was dissolved in water (115 mL). 5.4 mL of this solution was used to dissolve potassium osmium (VI) oxide dihydrate (240 mg) to get a purple suspension. The rest of the sodium hydroxide solution was treated with t-butyl carbamate (5.580 g, 47.1 mmol) in n-propanol (54 mL), followed by addition of t-butyl hypochlorite (5.4 mL, 47.1 mmol). This solution was stirred for 5 min, then (DHQD)2PHAL (630 mg) in n-propanol (54 mL) was added, followed by a solution of 2-vinylnaphthalene (2.5 g, 16 mmol) in n-propanol (54 mL) and a solution of potassium osmium (VI) oxide dihydrate previously made. The reaction mixture was stirred at room temperature for 0.5 hr. The reaction mixture was quenched with saturated NaHSO3 solution. After concentration, the residue was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, concentrated under vacuum. The crude product was purified by flash chromatography with 20% ethyl acetate in hekanes to give the title compound (2.6 g) as a solid.

1. customto get a purple suspension
2. stirringThe reaction mixture was stirred at room temperature for 0.5 hr
3. customThe reaction mixture was quenched with saturated NaHSO3 solution
4. concentrationAfter concentration
5. extractionthe residue was extracted with ethyl acetate
6. dry with materialThe combined organic layer was dried over magnesium sulfate
7. concentrationconcentrated under vacuum
8. customThe crude product was purified by flash chromatography with 20% ethyl acetate in hekanes