反应详情

To a solution of 3-nitro-napthalene-1-carbonyl chloride (8.4 g, 35.7 mmol) in anhydrous THF (70 mL) was added an ethereal solution of diazomethane (250 mL) dropwise at 0° C. The reaction mixture was stirred for 5 h, and then warmed to RT overnight. Excess diazomethane was decomposed by the dropwise addition of AcOH (50 mL). The mixture was extracted with Et2O (3×150 ml), washed with brine and saturated NaHCO3 aqueous solution, dried and filtered. The filtrate was concentrated to give the crude product, which was purified by column chromatography to yield 2-diazo-1-(3-nitronaphthalen-1-yl)ethanone (7.0 g, 81% yield). 1H NMR (300 MHz, DMSO-d6): δ 9.14 (s, 1H), 8.47 (d, J=7.2 Hz, 1H), 8.35 (d, J=7.2 Hz, 1H), 8.35 (s, 1H), 7.84 (t, J=7.2 Hz, 2H), 7.76 (t, J=7.8 Hz, 2H), 6.84 (s, 1H); MS (ESI) m/z: 242 (M+H+).

1. extractionThe mixture was extracted with Et2O (3×150 ml)
2. washwashed with brine and saturated NaHCO3 aqueous solution
3. customdried
4. filtrationfiltered
5. concentrationThe filtrate was concentrated
6. customto give the crude product, which
7. customwas purified by column chromatography