反应详情

A mixture of methyl 4-hydroxybenzoate (3 g, 19.7 mmol), 4-phenylbutanol (3.04 ml, 19.7 mmol) and triphenylphosphine (7.74 g, 29.6 mmol) in anhydrous tetrahydrofuran (110 ml) was added with diethyl azodicarboxylate (4.65 ml, 29.6 mmol). The resulting mixture was left under stirring at room temperature for 36 h, then was added with ethyl ether (500 ml) and left to crystallize for 24 hours at 0° C. After that the solid was filtered and the filtrate was washed successively with 0.2M hydrochloric acid, 5% sodium bicarbonate and a sodium chloride saturated solution. After drying and removing the solvent under reduced pressure, a residue was obtained which was purified by chromatography through a silica gel column, eluting with petroleum ether:chloroform mixtures of increasing polarity, thereby recovering 3.856 g of the title compound (70% yield).

1. waitThe resulting mixture was left
2. waitleft
3. customto crystallize for 24 hours at 0° C
4. filtrationAfter that the solid was filtered
5. washthe filtrate was washed successively with 0.2M hydrochloric acid, 5% sodium bicarbonate
6. customAfter drying
7. customremoving the solvent under reduced pressure
8. customa residue was obtained which
9. customwas purified by chromatography through a silica gel column
10. washeluting with petroleum ether
11. temperaturechloroform mixtures of increasing polarity