反应详情

To a mixture of methyl(6-hydroxy-4-(trifluoromethyl)-1-benzothiophen-3-yl)acetate (60 mg) and THF (dry) (2 mL) were added (2,6-dimethylpyridin-3-yl)methanol (31.2 mg), ADDP (62.6 mg), and tri-n-butylphosphine (0.153 mL) at room temperature. After stirring at room temperature for 16 h, the insoluble material was removed by filtration. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane). To the mixture of crude material and THF (1 mL) was added 1N NaOH (1 mL) at room temperature, and the mixture was stirred at room temperature for 13 h. The mixture was neutralized with 1N HCl at 0° C. and extracted with EtOAc. The organic layer was separated, washed successively with water and brine, dried over MgSO4 and concentrated in vacuo. The residual solid was crystallized from EtOAc-hexane to give the title compound (71.0 mg).

1. customthe insoluble material was removed by filtration
2. concentrationThe filtrate was concentrated in vacuo
3. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
4. additionTo the mixture of crude material and THF (1 mL)
5. additionwas added 1N NaOH (1 mL) at room temperature
6. stirringthe mixture was stirred at room temperature for 13 h
7. customwas neutralized with 1N HCl at 0° C.
8. extractionextracted with EtOAc
9. customThe organic layer was separated
10. washwashed successively with water and brine
11. dry with materialdried over MgSO4
12. concentrationconcentrated in vacuo
13. customThe residual solid was crystallized from EtOAc-hexane