反应详情

温度

60 °C

To a solution of ethyl (2E)-3-{4-[(3-fluoro-4-hydroxyphenyl)(cycloheptylidene)methyl]phenyl}-2-propenoate (134) (0.22 g, 0.56 mmol) in a mixture of EtOH (6 mL) and THF (6 mL) was added an aqueous solution of 1 N NaOH (7 mL). The mixture was stirred at 60° C. for 2 h. Upon cooling, the mixture was acidified to pH=2 with an aqueous solution of 2 N HCl. The mixture was extracted with EtOAc (2×50 mL). The combined organic extract was washed with brine and dried over Na2SO4. Upon concentration, light brown foam was obtained. It was triturated with hexanes (contains 1% MeOH) to give compound 135 as a pale yellow solid (0.171 g, 84%). mp 164-165° C. 1H NMR (400 MHz, DMSO-d6): δ 1.51 (br s, 8H), 2.10-2.30 (m, 4H), 6.45 (d, J=15.9 Hz, 1H), 6.70-6.78 (m, 1H), 6.80-6.90 (m, 1H), 7.14 (d, J=8.2 Hz, 2H), 7.53 (d, J=16.2 Hz, 1H), 7.59 (d, J=8.0 Hz, 2H), 9.74 (s, 1H), 12.35 (s, 1H). LCMS (ES): m/z 367 (M+H)+, m/z 365 (M−H)−. Anal. Calcd for C23H23FO3.0.1H2O: C, 75.02; H, 6.35; Found: C, 74.93; H, 6.44.

1. temperatureUpon cooling
2. extractionThe mixture was extracted with EtOAc (2×50 mL)
3. extractionThe combined organic extract
4. washwas washed with brine
5. dry with materialdried over Na2SO4
6. concentrationUpon concentration
7. customlight brown foam was obtained
8. customIt was triturated with hexanes (contains 1% MeOH)