反应详情

To a solution of 3-chloromethyl-5-(4-methoxy-phenyl)-[1,2,4]oxadiazole (8.90 mmol) in N,N-dimethylformamide (10 mL) was added sodium azide (17.8 mmol). This mixture was stirred at room temperature for 20 hours. The reaction mixture was poured into water (30 mL) and extracted with dichloromethane (3×). The combined organic extracts were combined and washed with water (2×), dried over anhydrous sodium sulfate, and evaporated. Then clear oily residue was placed under high vacuum and gently warmed for 18 hours. Upon cooling the material solidified. This solid was dissolved in tetrahydrofuran (15 mL) and treated with triphenylphosphine (9.0 mmol). Bubbling was immediately evident. This mixture was stirred for 16 hours and then treated with water (3.0 mL). This was heated in a 45° C. oil bath for 3 hours. The product was purified by flash chromatography (silica gel; 2:1 ether/dichloromethane), m.p. 66-68° C.

1. extractionextracted with dichloromethane (3×)
2. washwashed with water (2×)
3. dry with materialdried over anhydrous sodium sulfate
4. customevaporated
5. temperaturegently warmed for 18 hours
6. temperatureUpon cooling the material solidified
7. dissolutionThis solid was dissolved in tetrahydrofuran (15 mL)
8. customBubbling
9. stirringThis mixture was stirred for 16 hours
10. additiontreated with water (3.0 mL)
11. temperatureThis was heated in a 45° C. oil bath for 3 hours
12. customThe product was purified by flash chromatography (silica gel; 2:1 ether/dichloromethane), m.p. 66-68° C.