反应详情

温度

65 °C

To a solution of 3-{4-[cycloheptylidene-(4-hydroxy-phenyl)-methyl]-3-fluoro-phenyl}acrylic acid ethyl ester (176) (0.8 g, 2.15 mmol) in THF (10 mL) and ethanol (10 mL) was added 1 N sodium hydroxide (21 mL). The reaction mixture was heated at 65° C. for 2.5 h. The reaction mixture was partially concentrated to remove the EtOH and THF. To the basic aqueous mixture was added 1 N HCl to pH˜1 (according to litmus paper). The acidic aqueous solution was extracted with dichloromethane and the organic extract was washed with brine, dried over Na2SO4, filtered and concentrated. The crude material was triturated with dichloromethane, filtered and dried to give 0.065 g (10%) of compound 177 as a white powder. 1H NMR (400 MHz, DMSO-d6): δ 1.51 (b, 8H), 2.09 (m, 2H), 2.25 (m, 2H), 6.52 (d, J=16.1 Hz, 1H), 6.65 (d, J=8.4 Hz, 2H), 6.92 (d, J=8.4 Hz, 2H), 7.19 (t, J=7.8 Hz, 1H), 7.43-7.49 (m, 1H), 7.51-7.53 (m, 2H), 9.32 (s, 1H), 12.43 (s, 1H). HRMS (ESI) Calcd for C23H22FO3: 365.1553 (M−H)−. Found: 365.1543.

1. concentrationThe reaction mixture was partially concentrated
2. customto remove the EtOH and THF
3. additionTo the basic aqueous mixture was added 1 N HCl to pH˜1 (according to litmus paper)
4. extractionThe acidic aqueous solution was extracted with dichloromethane
5. extractionthe organic extract
6. washwas washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated
10. customThe crude material was triturated with dichloromethane
11. filtrationfiltered
12. customdried