反应详情

温度

0 °C

A mixture of methyl-4-(1,5-dibenzyl-1,4-dihydro-4-oxopyridin-3-yl)-2-hydroxy-4-oxobut-2-enoate 15, (0.080 g, 0.19 mmol) and 1 N NaOH (4 mL) in THF (12 mL) was stirred at 0° C. for 4 h. THF was distilled off and the residue acidified with 1 N HCl and extracted with EtOAc (2×25 mL), washed with brine solution (1×25 mL), dried over anhydrous Na2SO4 and EtOAc distilled off to give a yellow solid. The crude solid was triturated with diethylether, filtered and dried under vacuum. Finally the solid was triturated with chloroform, filtered and dried under vacuum for 24 h. Yield 0.065 g (84%), yellow solid, mp 140-142° C. 1H NMR (CDCl3+MeOH-d4, 500 MHz): δ 3.80 (s, 2H, CH2), 4.97 (s, 2H, CH2), 6.95 (t, 1H, CH, J=1 Hz), 7.13-7.40 (m, 11H, Ar—H and olefenic CH), 8.36 (d, 1H, CH, J=2.5 Hz). 13C NMR (CDCl3, 125 MHz): δ 33.4, 61.2, 120.5, 126.5, 127.5, 127.6, 128.6, 128.7, 128.7, 129.1, 129.1, 129.2, 129.2, 129.2, 129.4, 133.8, 135.9, 137.2, 138.2, 143.8, 163.8, 175.4. HRMS (M+H)+ calcd for C23H20NO5 390.1341, found 390.1343.

1. distillationTHF was distilled off
2. extractionextracted with EtOAc (2×25 mL)
3. washwashed with brine solution (1×25 mL)
4. dry with materialdried over anhydrous Na2SO4 and EtOAc
5. distillationdistilled off
6. customto give a yellow solid
7. customThe crude solid was triturated with diethylether
8. filtrationfiltered
9. customdried under vacuum
10. customFinally the solid was triturated with chloroform
11. filtrationfiltered
12. customdried under vacuum for 24 h