Ethyl Acetate → HCID 68872445, compound

To a solution of 2-[4-(3-benzoyloxypropyl)benzyl]-3,5-dimethylphenol (0.72 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (2.3 g) in toluene (7 mL) and dichloromethane (3 mL) was added boron trifluoride diethyl ether complex (0.73 mL), and the mixture was stirred at room temperature for 10 hours. To the reaction mixture were added ethyl acetate and a saturated aqueous sodium hydrogen carbonate solution, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (6 mL) and tetrahydrofuran (4 mL), sodium methoxide (28% methanol solution, 0.19 mL) was added to the solution, and the mixture was stirred at 30° C. for 7.5 hours. To the reaction mixture were added ethyl acetate and water, and the organic layer was separated. The organic layer was washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (10 mL), sodium methoxide (28% methanol solution, 0.075 mL) was added to the solution, and the mixture was stirred at 30° C. for 14 hours. The reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1). 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-(3-hydroxypropyl)-benzyl]-3,5-dimethylphenyl β-D-glucopyranoside (0.58 g).

1. customa saturated aqueous sodium hydrogen carbonate solution, and the organic layer was separated
2. washThe organic layer was washed with brine
3. dry with materialdried over anhydrous sodium sulfate
4. customthe solvent was removed under reduced pressure
5. dissolutionThe residue was dissolved in methanol (6 mL)
6. additiontetrahydrofuran (4 mL), sodium methoxide (28% methanol solution, 0.19 mL) was added to the solution
7. stirringthe mixture was stirred at 30° C. for 7.5 hours
8. additionTo the reaction mixture were added ethyl acetate and water
9. customthe organic layer was separated
10. washThe organic layer was washed with brine
11. dry with materialdried over anhydrous sodium sulfate
12. customthe solvent was removed under reduced pressure
13. dissolutionThe residue was dissolved in methanol (10 mL)
14. additionsodium methoxide (28% methanol solution, 0.075 mL) was added to the solution
15. stirringthe mixture was stirred at 30° C. for 14 hours
16. customThe reaction mixture was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1)
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-5891b696f1654427afebda9603b2bb92

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07541341B2