反应详情

Lithium aluminum hydride (1.31 g) was suspended in tetrahydrofuran (150 ml) under a nitrogen atmosphere. A solution of 5-acetoxy-4,6-di-tert-butylbenzofuran (10 g) in tetrahydrofuran (100 ml) was added dropwise to the suspension under cooling with ice. After heating under reflux for 3 h, the mixture was cooled to room temperature and, after addition of water and 10% aqueous HCl (100 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 [8.3 g (yield, 98%)].

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)