反应详情

温度

50 °C

To a solution of 38 (2.0 g, 5.0 mol) in THF (10 mL) was added 6N HCl (10 mL, 59.9 mmol) dropwise. The reaction was aged at 20-25° C. for 5 h then concentrated to remove THF. The residue was diluted with MTBE and basified with K2CO3. A total of 3 mL of H2O was added to dissolve all solids. The organic layer was separated, washed with brine, and solvent-switched to IPAC. To one-third of the organic layer was added 4-methylbenzoic acid (0.27 g, 2.00 mmol). The solution was heated to 50° C. and 2-hydroxy-5-nitrobenzaldehyde (0.0028 g, 0.017 mmol) was added. The reaction was aged at 20-25° C. for 16 h. The resulting slurry was chilled in an ice bath to 2° C. and filtered. The solids were washed with IPAC and dried to give product 39 (0.38 g, 52%) as crystals. 1H NMR (500 MHz, DMSO-d6): δ 7.82 (d, J=8.0 Hz, 2H), 7.26 (d, J=7.9 Hz, 2H), 7.18-7.19 (m, 3H), 7.12 (d, J=7.5 Hz, 1H), 4.67 (dq, J=15.2, 9.7 Hz, 1H), 3.72-3.74 (m, 2H), 3.61-3.63 (m, 1H), 3.55 (dd, J=11.3, 6.7 Hz, 1H), 2.40 (dd, J=25.2, 12.9 Hz, 1H), 2.35 (s, 3H), 2.32 (s, 3H), 2.02 (dd, J=12.6, 6.7 Hz, 1H), 0.91 (d, J=6.4 Hz; 3H); 13C NMR (100 MHz, DMSO-d6): δ 172.7, 168.3, 142.4, 139.1, 136.1, 130.9, 130.5, 129.7, 129.3, 127.4, 127.2, 126.5, 125.6 (q, J=281 Hz), 56.2, 52.1, 45.0 (q, J=32.3 Hz), 38.5, 29.1, 21.5, 18.7, 14.2

1. concentrationthen concentrated
2. customto remove THF
3. additionThe residue was diluted with MTBE and basified with K2CO3
4. additionA total of 3 mL of H2O was added
5. dissolutionto dissolve all solids
6. customThe organic layer was separated
7. washwashed with brine, and solvent-switched to IPAC
8. waitThe reaction was aged at 20-25° C. for 16 h
9. temperatureThe resulting slurry was chilled in an ice bath to 2° C.
10. filtrationfiltered
11. washThe solids were washed with IPAC
12. customdried