反应详情

温度

60 °C

To a solution of Ethyl(2E)-3-{4-[(3-chloro-4-hydroxyphenyl)(2,2,6,6-tetramethyl tetrahydro-4H-pyran-4-ylidene)methyl]phenyl}-2-propenoate (131) (0.32 g, 0.70 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 washed with brine and dried over Na2SO4. Upon concentration and adding hexanes, the title compound 132 was obtained as a white powder (0.255 g, 85%). mp 118-121° C. 1H NMR (400 MHz, DMSO-d6): δ 1.10 (s, 6H), 1.12 (s, 6H), 2.11 (s, 2H), 2.13 (s, 2H), 6.47 (d, J=15.9 Hz, 1H), 6.85-7.00 (m, 2H), 7.08 (d, J=1.8 Hz, 1H), 7.19 (d, J=8.2 Hz, 2H), 7.54 (d, J=15.9 Hz, 1H), 7.62 (d, J=8.2 Hz, 2H), 10.15 (s, 1H), 12.36 (s, 1H). LCMS (ESI): m/z 425 (M−H)−. Anal. Calcd for C25H27ClO4.0.2H2O: C, 69.74; H, 6.41; Found: C, 69.82; H, 6.56.

1. temperatureUpon cooling
2. extractionThe mixture was extracted with EtOAc (2×50 mL)
3. extractionThe combined organic extract
4. washwashed with brine
5. dry with materialdried over Na2SO4
6. concentrationUpon concentration
7. additionadding hexanes