反应详情

To a stirred, cooled (about 0° C.) solution of 3-hydroxy-4-nitro benzoic acid methyl ester. (394 mg, 2.0 mmol), triphenyl phosphine (525 mg, 2.0 mmol), arid 3-(dimethylamino)-propanol (237 μL, 2.0 mmol) in dry tetrahydrofuran (5 mL) was added diisopropyl azodicarboxylate (394 μL, 2.0 mmol in 1 mL of tetrahydrofuran). After stirring for 12 hours, the reaction was diluted with hydrochloric acid (30 mL of a 1M solution) and extracted with ethyl acetate (2×50 mL). The aqueous solution was basified with 10% aqueous sodium carbonate (50 mL) and the product was extracted with ethyl acetate (3×100 mL). The ethyl acetate was washed with brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced pressure to provide the desired crude product (86% yield). 1H-NMR (400 MHz, CDCl3) δ7.81 (d, 1H), 7.78 (s, 1H), 7.65 (d, 1H, 4.23 (t, 2H), 3.91 (s, 3H),2.44 (t, 2H), 2.22 (s, 6H), 2.05 (m, 2H).

1. extractionextracted with ethyl acetate (2×50 mL)
2. extractionthe product was extracted with ethyl acetate (3×100 mL)
3. washThe ethyl acetate was washed with brine (1×30 mL)
4. dry with materialdried (MgSO4)
5. filtrationfiltered
6. concentrationThe filtered solution was concentrated under reduced pressure