反应详情

To a 2 L round-bottomed flask equipped with a magnetic stirrer and a N2 bubbler were added 2-nitro-3-methoxybenzaldehyde (125.7 g, 0.6939 mol), nitroethane (73 g, 0.97 mol), 18-C-6 (18 g), isopropanol (420 mL) and KF (20 g). The mixture was stirred at RT for 16 h. The solvent was removed under vacuum to give an oil. Isopropanol (100 mL) and water (250 mL) were added. The mixture was placed under vacuum to give a slurry. The slurry was stirred for 1 h and filtered. The cake was washed with water (4×100 mL) and dried to give 1-(2-nitro-3-methoxyphenyl)-2-nitropropanol as a diastereomeric mixture in a ratio of 3:2 (170.3 g, 96% yield). 1H NMR for major isomer (CDCl3) δ1.38 (d, J=6.9 Hz, 3H), 2.94 (s, 1H), 3.92 (s, 3H), 4.90 (m, 1H), 5.08 (d, J=8.6 Hz, 1H), 7.05-7.52 (m, 3H). 1H NMR for minor isomer (CDCl3) δ1.55 (d, J=6.9 Hz, 3H), 2.94 (s, 1H), 4.80 (m, 1H), 5.46 (d, J=3.0 Hz), 7.05-7.52 (m, 3H).

1. customTo a 2 L round-bottomed flask equipped with a magnetic stirrer
2. customThe solvent was removed under vacuum
3. customto give an oil
4. customto give a slurry
5. stirringThe slurry was stirred for 1 h
6. filtrationfiltered
7. washThe cake was washed with water (4×100 mL)
8. customdried