Acetic Acid → HCID 20708445, compound

Temperature

100 °C

3-(2-hydroxyethyl)-7-methoxy-2-methylbenzofuran (2.34 g) was dissolved in DMF (60 ml) and potassium t-butoxide (2.71 g) and n-propanethiol (2.2 ml) were added to the solution, followed by stirring the resulting solution at 100° C. for 5 hours. The reaction mixture was cooled to room temperature and acetic acid (3 ml) was added. The reaction solution was concentrated, and poured into water layer (100 ml). The aqueous layer was extracted twice with ethyl acetate (50 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. Sodium sulfate was removed by filtration and the solvent was removed under reduced pressure. The obtained residue was dissolved in DMF (50 ml), and potassium carbonate (1.66 g ) and methyl bromoacetate (1.7 ml) were added, followed by stirring the resulting solution at room temperature for 17.5 hours. The reaction solution was concentrated and poured into water layer (100 ml), followed by extraction twice with ether (50 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=2/1-1/1) using silica gel to obtain the desired compound (2.29 g, yield: 75%).

1. temperatureThe reaction mixture was cooled to room temperature
2. concentrationThe reaction solution was concentrated
3. additionpoured into water layer (100 ml)
4. extractionThe aqueous layer was extracted twice with ethyl acetate (50 ml)
5. washwashed with saturated brine
6. dry with materialby drying over sodium sulfate
7. customSodium sulfate was removed by filtration
8. customthe solvent was removed under reduced pressure
9. dissolutionThe obtained residue was dissolved in DMF (50 ml)
10. additionpotassium carbonate (1.66 g ) and methyl bromoacetate (1.7 ml) were added
11. stirringby stirring the resulting solution at room temperature for 17.5 hours
12. concentrationThe reaction solution was concentrated
13. additionpoured into water layer (100 ml)
14. extractionfollowed by extraction twice with ether (50 ml)
15. washwashed with saturated brine
16. dry with materialby drying over sodium sulfate
17. customAfter removing the sodium sulfate
18. filtrationby filtration
19. customthe solvent was removed under reduced pressure
20. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=2/1-1/1)

ORD record

ord-4173e4e378ec472e88efb1166923daaa

Source dataset

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06323235B1