反应详情

Under argon, a 1.60 M solution of n-butyllithium in hexane (2.5 mL, 4.1 mmol) was added to anhydrous tetrahydrofuran (7.0 mL) stirred in a dry ice-acetone bath, followed by dropwise addition of a solution of 4-ethoxy-1-iodo-3,5-dimethoxybenzene (570.0 mg, 1.85 mmol) in anhydrous tetrahydrofuran (1.5 mL). After the mixture was stirred for 20 minutes in the dry ice-acetone bath, triisopropyl borate (0.50 mL, 2.2 mmol) was added, and the mixture was additionally stirred for 20 minutes. The reaction mixture was stirred at room temperature for 1 hour, and concentrated under reduced pressure. To the residue, a 0.1 M aqueous sodium hydroxide (4.4 mL) solution was added. The aqueous solution was washed with chloroform, acidified by the addition of concentrated hydrochloric acid, and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Chloroform-hexane was added to the residue and the resulting precipitate was collected by filtration to afford the title compound as a colorless amorphous powder (162.0 mg, yield: 39%).

1. additionwas added
2. stirringthe mixture was additionally stirred for 20 minutes
3. stirringThe reaction mixture was stirred at room temperature for 1 hour
4. concentrationconcentrated under reduced pressure
5. additionTo the residue, a 0.1 M aqueous sodium hydroxide (4.4 mL) solution was added
6. washThe aqueous solution was washed with chloroform
7. additionacidified by the addition of concentrated hydrochloric acid
8. extractionextracted with chloroform
9. washThe organic layer was washed with brine
10. dry with materialdried over anhydrous sodium sulfate
11. concentrationconcentrated under reduced pressure
12. additionChloroform-hexane was added to the residue
13. filtrationthe resulting precipitate was collected by filtration