反应详情

温度

-78 °C

A flask is charged with 3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (230 mg, 1 mmol), purged with nitrogen and anhydrous THF (5 ml) added. The resulting solution is cooled to −78° C. and lithium diisopropylamide (1.8M solution in hexane/THF/ethyl benzene) (0.61 ml, 1.1 mmol) is added dropwise and the reaction stirred at −78° C. for a further 30 minutes. A solution of 3-chloromethyl-5-methyl isoxazole in THF (1 ml) is then added in one portion, and the reaction is allowed to warm to ambient temperature and stirred for a further 2 hours. The reaction is quenched by the addition of saturated ammonium chloride solution (20 ml), and extracted with ethyl acetate (2×20 ml). The combined organics are evaporated under reduced pressure and the residue is purified by flash chromatography to give 3-methoxy-5-(5-methyl-isoxazol-3-ylmethyl)-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (132 mg)

1. custompurged with nitrogen and anhydrous THF (5 ml)
2. additionadded
3. temperatureto warm to ambient temperature
4. stirringstirred for a further 2 hours
5. customThe reaction is quenched by the addition of saturated ammonium chloride solution (20 ml)
6. extractionextracted with ethyl acetate (2×20 ml)
7. customThe combined organics are evaporated under reduced pressure
8. customthe residue is purified by flash chromatography