反应详情

温度

0 °C

To a 0° C. solution of (6-bromo-benzo[b]thiophen-2-yl)-acetaldehyde (2.21 g; 8.66 mmol) in t-butyl alcohol (50 mL; 526.36 mmoles; 50.00 mL; 39.015 g) and 2-methyl-2-butene (20 mL; 188 mmol) is added a solution of sodium chlorite (6.27 g; 69.3 mmol) in water (20 mL) and a solution of sodium phosphate monobasic (4.20 g; 34.6 mmol) in water (10 mL). The reaction mixture is stirred at 0° C. for 12 hours while warming to room temperature. The mixture is extracted with EtOAc (50 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is dissolved in methanol (30 mL). Sulfuric acid (1.0 mL; 18.8 mmol) is added and the mixture is stirred at 95° C. for 4 hours. The mixture is neutralized with aqueous NaHCO3 and concentrated under reduced pressure. The residual aqueous mixture is extracted with EtOAc (50 mL×2). The combined organic layers are dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product is purified via flash chromatography eluting with 20% EtOAc/Hexanes. The appropriate fractions are combined and concentrated under reduced pressure to afford the title compound (1.51 g, 61%). ES/MS m/e (M+18):303.8; (M−1):284.7

1. temperaturewhile warming to room temperature
2. extractionThe mixture is extracted with EtOAc (50 mL×2)
3. dry with materialThe combined organic layers are dried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure
6. dissolutionThe crude product is dissolved in methanol (30 mL)
7. stirringthe mixture is stirred at 95° C. for 4 hours
8. concentrationconcentrated under reduced pressure
9. extractionThe residual aqueous mixture is extracted with EtOAc (50 mL×2)
10. dry with materialThe combined organic layers are dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure
13. customThe crude product is purified via flash chromatography
14. washeluting with 20% EtOAc/Hexanes
15. concentrationconcentrated under reduced pressure