反应详情

温度

70 °C

A mixture of 4 (28.9 g, 79.6 mmol) and KOH (35.7 g, 636.7 mmol) in degassed t-BuOH (300 mL) is heated at 70° C. overnight. LC/MS indicates the reaction is completed. The mixture is cooled to rt, and then partitioned between H2O and Et2O. The two layers are separated, and the aqueous layer was extracted with Et2O (2×). The combined organic layers are washed with H2O and brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant to give 16 g (91%) of 5 as a yellow liquid. 1H NMR (CDCl3) δ 8.47 (br s, 1H), 7.35-7.20 (m, 1H), 6.95-6.80 (m, 2H), 6.68 (d, J=2.5 Hz, 1H); 19F NMR (CDCl3) δ −57.63 (s, 3F), −136.10 (d, J=8.5 Hz, 1F); MS 220 (M+1, 100%), 200.

1. temperatureThe mixture is cooled to rt
2. custompartitioned between H2O and Et2O
3. customThe two layers are separated
4. extractionthe aqueous layer was extracted with Et2O (2×)
5. washThe combined organic layers are washed with H2O and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe crude material is purified on silica gel with heptane/EtOAc (100/0 to 60/40) as eluant