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), and 3-(dimethylamino)-propanol (237 μL, 2.0 mmol) in dry tertrahydrofuran (5 mL) was added diisopropyl azodicarboxylate (394 μL, 2.0 mmol in I 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) δ 7.81 (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