反应详情

4-(phenyldiazenyl)phenol (2.100 g; 10.60 mmol) and potassium tert-butoxide (1.247 g; 11.13 mmol) were placed in a dry, two-neck, round-bottom flask equipped with a magnetic stirring bar, a reflux condenser, and a rubber septum. The flask was evacuated and purged with dry argon, then 25 mL of anhydrous N,N-dimethylformamide was added while stirring. As soon as the solids disappeared, 11-bromo-1-undecene (2.44 mL; 2.595 g; 11.13 mmol) was added and the solution was quickly heated, and allowed to reflux for 10 min. Formation of white precipitate was observed, and the color of the solution changed from deep red to bright orange. After 10 min, the heating was discontinued, and the flask was allowed to cool down. The reaction mixture was poured into a separatory funnel containing 100 mL of water, and extracted with four 50 mL portions of hexane. Hexane fractions were combined and dried over magnesium sulfate. Hexane was removed on a rotary evaporator, and the residue was purified by column chromatography (ethyl acetate:hexane 1:20) to give 2.95 g (79.5%) of analytically pure product.

1. customequipped with a magnetic stirring bar, a reflux condenser
2. customThe flask was evacuated
3. custompurged with dry argon
4. addition25 mL of anhydrous N,N-dimethylformamide was added
5. temperaturethe solution was quickly heated
6. temperatureto reflux for 10 min
7. temperatureto cool down
8. additionThe reaction mixture was poured into a separatory funnel
9. extractionextracted with four 50 mL portions of hexane
10. dry with materialdried over magnesium sulfate
11. customHexane was removed on a rotary evaporator
12. customthe residue was purified by column chromatography (ethyl acetate:hexane 1:20)
13. customto give 2.95 g (79.5%) of analytically pure product