反应详情

To a stirred solution of 3-methyl-4-(1,3-thiazol-4-yl)phenyl trifluoromethanesulfonate from step 3 (2.60 g, 8.05 mmol) in dioxane (75 ml) was added tributyl(1-ethoxyvinyl)tin (3.5 g, 9.66 mmol), tetrakis(triphenylphosphine) palladium (930 mg, 0.805 mmol), lithium chloride (850 mg, 20.0 mmol), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, and diluted with ethyl acetate. The whole was washed with saturated potassium fluoride aqueous solution, and the precipitate was removed by filteration through celite. The resulting solution was extracted with ethyl acetate. The organic layer was concentrated in vacuo. To the residue was added THF (50 ml), 2N HCl aqueous solution (50 ml), and the mixture was heated at reflux temperature for 8 hours. The reaction mixture was cooled down to room temperature, made neutral by addition of NaHCO3, and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:5) to give title compound (714 mg, 41% yield).

1. temperaturethe mixture was heated
2. temperatureat reflux temperature for 8 hours
3. washThe whole was washed with saturated potassium fluoride aqueous solution
4. customthe precipitate was removed by filteration through celite
5. extractionThe resulting solution was extracted with ethyl acetate
6. concentrationThe organic layer was concentrated in vacuo
7. additionTo the residue was added THF (50 ml), 2N HCl aqueous solution (50 ml)
8. temperaturethe mixture was heated
9. temperatureat reflux temperature for 8 hours
10. temperatureThe reaction mixture was cooled down to room temperature
11. additionmade neutral by addition of NaHCO3
12. extractionextracted with ethyl acetate
13. washThe organic layer was washed with brine
14. dry with materialdried over MgSO4
15. concentrationconcentrated in vacuo
16. customThe residue was purified by flash chromatography
17. washeluting with ethyl acetate-hexane (1:5)