反应详情

A 300 ml-capacity three neck flask containing a stirring bar and connected to a condenser was sufficiently dried. Then, a nitrogen atmosphere was established in the flask. 1-nitro-4-(1,8-nonadiene-5-yloxy)benzene (11) (4.01 g, 1.4 mmol), an iron powder (3.13 g, 5.6 mmol), and ethanol (50%, 10 ml) were introduced into the flask, and the mixture thus obtained was started to be stirred while heating the flask in an oil bath. Further, HCl (0.52 ml) and ethanol (50%, 2.5 ml) were slowly added to the mixture, which was then stirred for 2 hours. Thereafter, an aqueous sodium hydroxide solution was added to the mixture to stop the reaction, and an organic layer was extracted with ethyl acetate. This organic layer was dried over Na2SO4 and filtered, a solvent was distilled of under reduced pressure, and the organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1). Thus, 1-amino-4(1,8-nonadiene-5-yloxy)benzene (12) (2.39 g, 9.64×10−3 mol, yield: 69%) was obtained as an intended compound.

1. additionA 300 ml-capacity three neck flask containing a stirring bar
2. customconnected to a condenser
3. customwas sufficiently dried
4. customthe mixture thus obtained
5. temperaturewhile heating the flask in an oil bath
6. stirringwas then stirred for 2 hours
7. customthe reaction
8. extractionan organic layer was extracted with ethyl acetate
9. dry with materialThis organic layer was dried over Na2SO4
10. filtrationfiltered
11. distillationa solvent was distilled of under reduced pressure
12. customthe organic layer was purified by flash chromatography on silica gel (hexane:ethyl acetate=10:1)