Potassium Carbonate → Methyl 3-(2-hydroxyethyl)-2,3-dihydrobenzofuran-7-yloxyacetate

7-hydroxy-3-(2-hydroxyethyl)benzofuran (7.01 g) was dissolved in dimethylformamide (100 ml), and potassium carbonate (5.76 g) and methyl bromoacetate (4.74 ml) were added to the resultant solution, and the mixture was stirred at room temperature for 21 hours. The reaction solution was filtered with Celite, and the filtrate was concentrated. Ethyl acetate (300 ml) was added to the residue, and then the mixture was washed with water and saturated brine, and dried over sodium sulfate. After sodium sulfate was filtered off, the filtrate was concentrated, and the residue was dissolved in methanol (100 ml). 5% Pd/C (1.0 g), and acetic acid (5 ml) were added to the resultant solution, and the mixture was stirred at room temperature for 23 hours under a hydrogen atmosphere. The reaction solution was filtered with Celite, and the filtrate was concentrated. Ethyl acetate (300 ml) was added to the residue, and the mixture was washed with water and saturated brine, and dried over sodium sulfate. After sodium sulfate was filtered off, the filtrate was concentrated, and the residue was purified by flash column chromatography using silica gel (elution solvent:hexane/ethyl acetate=1/2) to obtain the object compound (7.80 g, yield 74%).

1. filtrationThe reaction solution was filtered with Celite
2. concentrationthe filtrate was concentrated
3. additionEthyl acetate (300 ml) was added to the residue
4. washthe mixture was washed with water and saturated brine
5. dry with materialdried over sodium sulfate
6. filtrationAfter sodium sulfate was filtered off
7. concentrationthe filtrate was concentrated
8. dissolutionthe residue was dissolved in methanol (100 ml)
9. addition5% Pd/C (1.0 g), and acetic acid (5 ml) were added to the resultant solution
10. stirringthe mixture was stirred at room temperature for 23 hours under a hydrogen atmosphere
11. filtrationThe reaction solution was filtered with Celite
12. concentrationthe filtrate was concentrated
13. additionEthyl acetate (300 ml) was added to the residue
14. washthe mixture was washed with water and saturated brine
15. dry with materialdried over sodium sulfate
16. filtrationAfter sodium sulfate was filtered off
17. concentrationthe filtrate was concentrated
18. customthe residue was purified by flash column chromatography

ORD record

ord-b102efe757bc4980bf2f1ff8c96ff3ea

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06407096B1