Hydrochloric Acid → HCID 67136390, compound

To a suspension of 2′-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6′-methoxycarbonylmethoxy-4′-methylacetophenone (0.35 g) and p-tolualdehyde (81 mg) in ethanol (10 mL) were added water (1.7 mL) and potassium hydroxide (0.41 g), and the mixture was stirred at room temperature for 4 hours. The reaction mixture was poured into 1 mol/L hydrochloric acid (7.5 mL), and the resulting mixture was extracted with ethyl acetate twice. The extracts were combined and washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was dissolved in methanol (6 mL)-tetrahydrofuran (1 mL). To the solution was added 10% palladium-carbon powder (0.11 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. To the residue were added sodium acetate (1.15 g), acetic acid (6 mL) and acetic anhydride (1.16 mL), and the mixture was stirred at 115° C. overnight. The reaction mixture was cooled to room temperature and poured into water, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution twice, water and brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-6-methyl-3-[2-(4-methylphenyl)ethyl]benzofuran (0.11 g). This material was dissolved in methanol (5 mL). To the solution was added sodium methoxide (28% methanol solution, 0.036 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was purified by VARIAN BOND ELUT-SCX (eluent: methanol) to give the title compound (74 mg).

1. extractionthe resulting mixture was extracted with ethyl acetate twice
2. washwashed with brine
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe solvent was removed under reduced pressure
5. dissolutionthe residue was dissolved in methanol (6 mL)-tetrahydrofuran (1 mL)
6. additionTo the solution was added 10% palladium-carbon powder (0.11 g)
7. stirringthe mixture was stirred at room temperature under a hydrogen atmosphere for 2 hours
8. customThe insoluble material was removed by filtration
9. concentrationthe filtrate was concentrated under reduced pressure
10. additionTo the residue were added sodium acetate (1.15 g), acetic acid (6 mL) and acetic anhydride (1.16 mL)
11. stirringthe mixture was stirred at 115° C. overnight
12. temperatureThe reaction mixture was cooled to room temperature
13. additionpoured into water
14. extractionthe resulting mixture was extracted with ethyl acetate
15. washThe extract was washed with a saturated aqueous sodium hydrogen carbonate solution twice
16. dry with materialwater and brine successively, and dried over anhydrous magnesium sulfate
17. customThe solvent was removed under reduced pressure
18. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=2/1)

ORD record

ord-175f41d834e245cf82f7d7ff99447021

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07566699B2