Methyl iodide → 3-[1,3]Dioxolan-2-yl-6-methoxy-2-methyl-benzofuran

Temperature

-30 °C

3-(1,3-Dioxolan-2-yl)-6-methoxybenzofuran (0.144 g, 0.65 mmol) was dissolved in THF (5 mL) at −30 to −20° C. To this solution was added dropwise tert-butyllithium (15% in pentane, 0.56 mL, 1.31 mmol). The reaction mixture was continuously stirred at −30° C. for 30 min and then allowed to warm to 0° C. and stir for another 20 min. The reaction mixture was cooled to −30° C. again and iodomethane (0.138 g, 0.98 mmol) was added dropwise. After stirring at −30° C. for another 1 h, it was allowed to warm to room temperature overnight. After the solvent was removed under reduced pressure, the residue was dissolved in EtOAc and washed with saturated NaHCO3. The aqueous layer was extracted with EtOAc (3×20 mL). The combined organic layers were dried over anhydrous MgSO4 and concentrated under reduced pressure to provide 3-[1,3]dioxolan-2-yl-6-methoxy-2-methyl-benzofuran.

1. temperatureto warm to 0° C.
2. stirringstir for another 20 min
3. temperatureThe reaction mixture was cooled to −30° C. again
4. stirringAfter stirring at −30° C. for another 1 h
5. temperatureto warm to room temperature overnight
6. customAfter the solvent was removed under reduced pressure
7. dissolutionthe residue was dissolved in EtOAc
8. washwashed with saturated NaHCO3
9. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
10. dry with materialThe combined organic layers were dried over anhydrous MgSO4
11. concentrationconcentrated under reduced pressure

ORD record

ord-577fb68331b84506a28e3f51d50e3eda

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456289B2