反应详情

温度

75 °C

A stirred mixture of T10.3 (1.63 g, 4.420 mmol), ground S-Phos (0.36 g, 0.88 mmol), palladium acetate (0.10 g, 0.45 mmol), and potassium phosphate tribasic (2.35 g, 11.06 mmol) in DMF (13 mL) and water (0.4 mL) was purged three times with argon and placed under vacuum three times. 2-(5,5-Dimethylcyclopent-1-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (T2.2) (1.47 g, 6.63 mmol) was added to the mixture via syringe, and the resulting mixture was heated to 75° C. After 18 hours (black solution), the reaction was cooled to room temperature, diluted with water, and extracted three times with EtOAc. The combined organic layers were washed twice with brine. After drying over anhydrous sodium sulfate and filtration, the organic solvent was removed under reduced pressure. The residue was purified on a 40 g column of silica gel (0-10% EtOAc in hexanes) to afford T10.4 as a white solid (1.12 g, 66% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.69 (1H, dd, J=11.7, 2.3 Hz), 7.57 (1H, dd, J=2.0, 1.2 Hz), 7.31 (2H, m), 6.88 (2H, m), 5.56 (1H, t, J=2.5 Hz), 5.01 (2H, s), 3.91 (3H, s), 3.82 (3H, s), 2.42 (2H, td, J=7.0, 2.7 Hz), 1.86 (2H, t, J=7.2 Hz), 1.06 (6H, s).

1. customwas purged three times with argon
2. temperaturethe reaction was cooled to room temperature
3. extractionextracted three times with EtOAc
4. washThe combined organic layers were washed twice with brine
5. dry with materialAfter drying over anhydrous sodium sulfate and filtration
6. customthe organic solvent was removed under reduced pressure
7. customThe residue was purified on a 40 g column of silica gel (0-10% EtOAc in hexanes)