反应详情

温度

100 °C

To a stirred solution of the triflate (from example 10) (9.35 g, 21.6 mmol) and tetrakis-(triphenylphosphine)palladium(0) (750 mg, 0.65 mmol) in toluene (70 mL) was added a solution of 4-formylphenylboronic acid (4.06 g, 27.05 mmol) in ethanol (20 mL) and 2N sodium carbonate (21.6 mL, 43.2 mmol). The resulting suspension was stirred at 100° C. for 4 hrs (TLC control). The reaction was cooled, diluted with water (50 mL) and extracted with diethyl ether (3×100 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The resulting brown solid was redissolved in tetrahydrofuran (50 mL). 2N Hydrochloric acid (10 mL) was added and the resulting solution was stirred at room temperature for 1 hour, and then diluted with water (50 mL) and extracted with diethyl ether (3×100 mL). The combined extract was washed with water, brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification of the product by flash column chromatography, using 20% ethyl acetate in heptane as eluent, afforded the title compound as a white solid (7.34 g, 88%).

1. temperatureThe reaction was cooled
2. extractionextracted with diethyl ether (3×100 mL)
3. extractionThe combined extract
4. washwas washed with water, brine
5. dry with materialdried over anhydrous MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThe resulting brown solid was redissolved in tetrahydrofuran (50 mL)
9. addition2N Hydrochloric acid (10 mL) was added
10. stirringthe resulting solution was stirred at room temperature for 1 hour
11. additiondiluted with water (50 mL)
12. extractionextracted with diethyl ether (3×100 mL)
13. extractionThe combined extract
14. washwas washed with water, brine
15. dry with materialdried over anhydrous MgSO4
16. filtrationfiltered
17. concentrationconcentrated in vacuo
18. customPurification of the product by flash column chromatography