Ethyl Acetate → HCID 69014763, compound

HRID 2375144Notes

Reaction equation

HRID 2375144 reaction equation
[CH2:1]([S:3][C:4]1[CH:17]=[CH:16][C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])=[CH:6][CH:5]=1)[CH3:2].C(O[C@@H:22]1[O:39][C@H:38]([CH2:40][O:41]C(=O)C)[C@@H:33]([O:34]C(=O)C)[C@H:28]([O:29]C(=O)C)[C@H:23]1[O:24]C(=O)C)(=O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1.ClCCl>[O:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[CH2:8][C:7]1[CH:16]=[CH:17][C:4]([S:3][CH2:1][CH3:2])=[CH:5][CH:6]=1)[C@@H:22]1[O:39][C@H:38]([CH2:40][OH:41])[C@@H:33]([OH:34])[C@H:28]([OH:29])[C@H:23]1[OH:24]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 2724702beta-D-Glucose pentaacetateHCID 12134582HCID 12134582, compound

Product 1

HCID 69014763HCID 69014763, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-ethylthiobenzyl)phenol (0.51 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (2.4 g) in toluene (6.3 mL) and dichloromethane (2.7 mL) was added boron trifluoride diethyl ether complex (0.78 mL), and the mixture was stirred at room temperature for 9 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), dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (10.5 mL), sodium methoxide (28% methanol solution, 0.08 mL) was added to the solution, and the mixture was stirred at 25° C. for 18 hours. To the reaction mixture were added ethyl acetate (75 mL) and water (20 mL), and the organic layer was separated. The organic layer was washed with brine (20 mL), dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1). The solvent was removed under reduced pressure, diethyl ether was added to the residue, and the resulting precipitates were collected by filtration. The obtained colorless solid was washed with diethyl ether and dried under reduced pressure to give 2-(4-ethylthiobenzyl)phenyl β-D-glucopyranoside (0.51 g).

Workup

  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 (10.5 mL)
  6. additionsodium methoxide (28% methanol solution, 0.08 mL) was added to the solution
  7. stirringthe mixture was stirred at 25° C. for 18 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 was washed with brine (20 mL)
  11. dry with materialdried over anhydrous sodium sulfate
  12. customthe solvent was removed under reduced pressure
  13. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)
  14. customThe solvent was removed under reduced pressure, diethyl ether
  15. additionwas added to the residue
  16. customthe resulting precipitates
  17. filtrationwere collected by filtration
  18. washThe obtained colorless solid was washed with diethyl ether
  19. customdried under reduced pressure

Sources & evidence

ORD record
ord-77a966fe41364cd5bac706ae5e87bf2a
Source dataset
uspto-grants-2008_12
Patent number
US07465712B2

Reaction notes

Loading…