反应详情

温度

0 °C

To a mixture of 3-hydroxy-2,5-dimethylphenyl acetate (1.04 g) and CH3CN (57 mL) were added TEA (1.61 mL) and Tf2O (1.17 mL) at 0° C. The mixture was stirred at 0° C. for 30 min under nitrogen atmosphere. The mixture was diluted with water at 0° C. and then concentrated in vacuo. The residue was extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residual crude material was dissolved in toluene (50 mL). To the solution were added DIPEA (1.79 mL), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.150 g), (4-methoxyphenyl)methanethiol (0.723 mL) and tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, 0.238 g) at room temperature. The mixture was refluxed for 4 h. After cooling, water was added to the mixture, and the mixture was extracted with EtOAc. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (1.27 g).

1. concentrationconcentrated in vacuo
2. extractionThe residue was extracted with EtOAc
3. washThe organic layer was washed with brine
4. dry with materialdried over MgSO4
5. concentrationconcentrated in vacuo
6. dissolutionThe residual crude material was dissolved in toluene (50 mL)
7. additionTo the solution were added DIPEA (1.79 mL), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.150 g), (4-methoxyphenyl)methanethiol (0.723 mL) and tris(dibenzylideneacetone)dipalladium (0) (Pd2(dba)3, 0.238 g) at room temperature
8. temperatureThe mixture was refluxed for 4 h
9. temperatureAfter cooling
10. additionwater was added to the mixture
11. extractionthe mixture was extracted with EtOAc
12. customThe organic layer was separated
13. washwashed with brine
14. dry with materialdried over MgSO4
15. concentrationconcentrated in vacuo
16. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)