Sodium Bicarbonate → HCID 68872067, compound

HRID 1826657Notes

Reaction equation

HRID 1826657 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:24]=[CH:23][C:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[OH:22])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C@@H:29]1[O:46][C@H:45]([CH2:47][O:48]C(=O)C)[C@@H:40]([O:41]C(=O)C)[C@H:35]([O:36]C(=O)C)[C@H:30]1[O:31]C(=O)C)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.ClCCl>[O:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[CH2:15][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:24][CH:23]=1)[C@@H:29]1[O:46][C@H:45]([CH2:47][OH:48])[C@@H:40]([OH:41])[C@H:35]([OH:36])[C@H:30]1[OH:31]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724702beta-D-Glucose pentaacetateHCID 12085584HCID 12085584, compound

Product 1

HCID 68872067HCID 68872067, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(2-benzyloxyethyl)benzyl]phenol (3.2 g) and 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (12 g) in toluene (34 mL) and dichloromethane (17 mL) was added boron trifluoride diethyl-ether complex (3.8 mL), and the mixture was stirred at room temperature for 14 hours. A saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (50 mL), sodium methoxide (28% methanol solution, 0.39 mL) was added to the solution, and the mixture was stirred at room temperature for 2.5 hours. The solvent of the reaction mixture was removed under reduced pressure, water was added to the residue, and the resulting mixture was extracted with ethylacetate. The organic layer was washed with brine and 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) to give 2-[4-(2-benzyloxyethyl)benzyl]phenyl β-D-glucopyranoside (3.4 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe residue was dissolved in methanol (50 mL)
  6. additionsodium methoxide (28% methanol solution, 0.39 mL) was added to the solution
  7. stirringthe mixture was stirred at room temperature for 2.5 hours
  8. customThe solvent of the reaction mixture was removed under reduced pressure, water
  9. additionwas added to the residue
  10. extractionthe resulting mixture was extracted with ethylacetate
  11. washThe organic layer was washed with brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. customthe solvent was removed under reduced pressure
  14. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-4fd77e41f4fa4b65b8c14ee2647b715f
Source dataset
uspto-grants-2006_05
Patent number
US07053060B2

Reaction notes

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