反应详情

A solution of 2-(4-tert-butylphenyl)ethanol (5.35 g, 30.0 mmol) in chloroform (150 mL) was cooled in ice and Dess-Martin periodinane (16.5 g, 39.0 mmol) was added thereto. The mixture was warmed to room temperature and stirred for 3 hr. The reaction mixture was diluted with chloroform (150 mL), followed by cooling in ice. Thereafter, saturated aqueous sodium thiosulfate solution was added thereto and the mixture was stirred for 5 min. The mixture was extracted three times with chloroform and then the organic layer was washed with brine and dried over anhydrous magnesium sulfate. The desiccant was filtered off and then the filtrate was concentrated under reduced pressure. The resulting precipitate was filtered again, followed by washing with chloroform. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford the title compound as a yellow oil (4.24 g).

1. temperatureby cooling in ice
2. stirringthe mixture was stirred for 5 min
3. extractionThe mixture was extracted three times with chloroform
4. washthe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe desiccant was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. filtrationThe resulting precipitate was filtered again
9. washby washing with chloroform
10. concentrationThe filtrate was concentrated under reduced pressure
11. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)