反应详情

温度

-78 °C

To a solution of 2-tert-butyl-6-methylphenol (1.2 g, 7.3 mmol) in methylene chloride (28 ml, 1.1 equiv.), stirred under argon at -78° C., is added 5-hexynoyl chloride (1.0 g) followed by tin tetrachloride (0.93 mL, 1.1 equiv.). After stirring 30 minutes at -78° C., the reaction is warmed to -50° C. and stirred 5 minutes more. The mixture is then quenched with 1N HCl/ether. The product is extracted from 1N HCl with 3 portions of ether, and the ether layers are combined and washed with water. The resulting ether layer is dried (MgSO4), filtered, and concentrated in vacuo to give 2.14 g crude product. The product is flash chromatographed on silica gel using 10% EtOAc in hexane to give 0.97 g 2-t-butyl-4-(5-hexynoyl)-6-methylphenol. Crystallization from hexane gives crystals, mp 63°-64° C.

1. temperaturethe reaction is warmed to -50° C.
2. stirringstirred 5 minutes more
3. customThe mixture is then quenched with 1N HCl/ether
4. extractionThe product is extracted from 1N HCl with 3 portions of ether
5. washwashed with water
6. dry with materialThe resulting ether layer is dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customto give 2.14 g crude product
10. customchromatographed on silica gel using 10% EtOAc in hexane