Ethyl Acetate → HCID 68871711, compound

Temperature

25 °C

To a solution of 2-[4-(2-benzoyloxyethyl)benzyl]phenol (0.49 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (1.7 g) in toluene (5.2 mL) and dichloromethane (2.2 mL) was added boron trifluoride diethyl ether complex (0.56 mL), and the mixture was stirred at 25° C. for 8 hours. To the reaction mixture were added ethyl acetate (70 mL) and a saturated aqueous sodium hydrogen carbonate solution (25 mL), and the organic layer was separated. The organic layer was washed with brine (25 mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (5 mL) and tetrahydrofuran (2.5 mL), sodium methoxide (28% methanol solution, 0.14 mL) was added to the solution, and the resulting mixture was stirred at 25° C. for 12.5 hours. To the reaction mixture were added ethyl acetate (75 mL) and water (20 mL), and the organic layer was separated. The organic layer as washed with brine (20 mL) and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (7.5 mL), sodium methoxide (28% methanol solution, 0.085 mL) was added to the solution, and the resulting mixture was stirred at 25° C. for 5 hours. The reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=4/1). The solvent was removed under reduced pressure, diethyl ether was added to the residue, and the resulting precipitates were collected by filtration. The obtained solid was washed with diethyl ether and dried under reduced pressure to give 2-[4-(2-hydroxyethyl)benzyl]phenyl β-D-glucopyranoside (0.47 g).

1. customa saturated aqueous sodium hydrogen carbonate solution (25 mL), and the organic layer was separated
2. washThe organic layer was washed with brine (25 mL)
3. dry with materialdried over anhydrous sodium sulfate
4. customthe solvent was removed under reduced pressure
5. dissolutionThe residue was dissolved in methanol (5 mL)
6. additiontetrahydrofuran (2.5 mL), sodium methoxide (28% methanol solution, 0.14 mL) was added to the solution
7. stirringthe resulting mixture was stirred at 25° C. for 12.5 hours
8. additionTo the reaction mixture were added ethyl acetate (75 mL) and water (20 mL)
9. customthe organic layer was separated
10. washThe organic layer as washed with brine (20 mL)
11. dry with materialdried over anhydrous sodium sulfate
12. customthe solvent was removed under reduced pressure
13. dissolutionThe residue was dissolved in methanol (7.5 mL)
14. additionsodium methoxide (28% methanol solution, 0.085 mL) was added to the solution
15. stirringthe resulting mixture was stirred at 25° C. for 5 hours
16. customThe reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=4/1)
17. customThe solvent was removed under reduced pressure, diethyl ether
18. additionwas added to the residue
19. customthe resulting precipitates
20. filtrationwere collected by filtration
21. washThe obtained solid was washed with diethyl ether
22. customdried under reduced pressure

ORD record

ord-8430e56b72a848449c7acaee21da5bcd

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07465712B2