反应详情

温度

40 °C

To 50 ml of a glacial acetic acid solution containing 600 mg of 4-[4-(t-butyldimethylsilyl)oxy-1,2-epoxy-2,6,6-trimethylcyclohexyl]but-3-en-2-one was added 8.9 g of a zinc powder at room temperature, and the mixture was vigorously stirred for 5 hours while maintaining the reaction temperature at about 40° C. To the reaction mixture was added 120 ml of chloroform, followed by stirring vigorously. Any insoluble matter was separated by filtration, and the filtrate was washed successively with water, a 5% aqueous solution of sodium hydrogen carbonate and water. The organic layer was dried over anhydrous magnesium sulfate, and the solvent, etc. were removed by distillation under reduced pressure. Purification of the resiude by silica gel chromatography gave 241 mg (yield: 55%) of 4-(2,4-dihydroxy-2,6,6-trimethylcyclohexyl)but-3-en-2-one.

1. stirringby stirring vigorously
2. customAny insoluble matter was separated by filtration
3. washthe filtrate was washed successively with water
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent, etc. were removed by distillation under reduced pressure
6. customPurification of the resiude by silica gel chromatography