反应详情

Ammonia (300 mL) was condensed in a flask containing 8-Acetamido-2-methoxynaphthalene (24.5 g, 115 mmol), t-butyl alcohol (34 g, 0.46 mol) and THF (300 mL). Sodium (8 g, 0.35 mol) was added in portions and the mixture was stirred for 3 h and allowed to warm to room temperature. The mixture was poured onto ice and saturated sodium chloride, and then extracted with THF (3×). The combined organic layers were washed with saturated sodium chloride, dried over magnesium sulfate, filtered and evaporated to give a dark solid. The residue was dissolved in 50% acetic acid and heated at 95° C. for 18 h. After evaporation, the residue was suspended in dimethyl ether and collected by filtration and dried. The filtrate was purified by silica gel chromatography (3:2 EtOAc:hexane) and combined with the other product to give a tan solid (10 g).

1. customcondensed in a flask
2. extractionextracted with THF (3×)
3. washThe combined organic layers were washed with saturated sodium chloride
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. customevaporated
7. customto give a dark solid
8. temperatureheated at 95° C. for 18 h
9. customAfter evaporation
10. filtrationcollected by filtration
11. customdried
12. customThe filtrate was purified by silica gel chromatography (3:2 EtOAc:hexane)