反应详情

81 g (1.24 mol) of zinc powder were added to a solution of 25.19 g (77.9 mmol) of 2-t-butyl-5-(t-butyldimethylsilyloxymethyl)-1-nitrobenzene (prepared as described in Preparation 11) in 270 ml of methanol, and then 10.8 ml of acetic acid were added to the resulting mixture, with ice-cooling. After the exothermic reaction had subsided, the reaction mixture was heated under reflux for 3 hours and then allowed to cool to room temperature, after which it was filtered using a Celite (trade mark) filter aid, and the zinc used was washed with methanol. The filtrate was combined with the washings and the combined mixture was concentrated by evaporation under reduced pressure. The concentrate was dissolved in ethyl acetate, and the resulting solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure, to give 22.9 g (a quantitative yield) of the title compound as an oily substance. The compound could be used without purification.

1. temperaturecooling
2. customAfter the exothermic reaction
3. temperaturethe reaction mixture was heated
4. temperatureunder reflux for 3 hours
5. filtrationafter which it was filtered
6. filtrationfilter aid
7. washthe zinc used was washed with methanol
8. concentrationthe combined mixture was concentrated by evaporation under reduced pressure
9. dissolutionThe concentrate was dissolved in ethyl acetate
10. washthe resulting solution was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
11. dry with materialafter which it was dried over anhydrous sodium sulfate
12. customThe solvent was removed by distillation under reduced pressure