反应详情

Lithium aluminum hydride (0.26 g) was suspended in tetrahydrofuran (50 ml) under a nitrogen atmosphere and a solution of 5-acetoxy-4,6-di-tert-butyl-2-octylbenzofuran (2.7 g) in tetrahydrofuran (20 ml) was added to the suspension under cooling with ice. After heating under reflux for 3 h, the mixture was cooled to room temperature and water was added dropwise. After adding 10% aqueous HCl (50 ml), the mixture was subjected to extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane) to afford 4,6-di-tert-butyl-5-hydroxybenzofuran [2.2 g (yield, 92%)] as a colorless oil.

1. temperatureunder cooling with ice
2. temperatureAfter heating
3. temperatureunder reflux for 3 h
4. extractionthe mixture was subjected to extraction with ethyl acetate
5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
6. concentrationconcentrated
7. customThe concentrate was purified by silica gel chromatography (10% ethyl acetate in n-hexane)