Ethyl Acetate → HCID 10623633, compound

HRID 1760729Notes

Reaction equation

HRID 1760729 reaction equation
[C:1]([O:4][C@@H:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)[CH3:2].C([Br:31])CO.C(OCC)(=O)C>ClCCl>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][C@H:5]1[O:4][CH2:1][CH2:2][Br:31])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 108982-BromoethanolHCID 2724702beta-D-Glucose pentaacetate

Product 1

HCID 10623633HCID 10623633, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 9.46 g (24.3 mmol) of penta-O-acetyl-β-D-glucopyranose and 3.04 g (24.3 mmol) of ethylene bromohydrin in 100 mL of dichloromethane was put in a 200 mL round bottom flask in an argon atmosphere. Subsequently, 10 mL of boron trifluoride diethyl ether complex was slowly added dropwise to this solution with stirring. The resulting mixture was continuously stirred with ice cooling for another one hour and then stirred at room temperature overnight while protecting it from light. After the stirring, the color of the reaction solution turned orange. An adequate amount of ethyl acetate was added to the reaction solution, and the organic phase was washed with water, a saturated aqueous sodium hydrogen carbonate and a saturated saline successively. After the organic solution was dried over anhydrous sodium sulfate, the organic phase was filtered, and the solvent was evaporated under reduced pressure to give 2-bromoethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside in the form of an oil (yield 11.0 g; 100%)

Workup

  1. additionSubsequently, 10 mL of boron trifluoride diethyl ether complex was slowly added dropwise to this solution
  2. stirringThe resulting mixture was continuously stirred with ice cooling for another one hour
  3. stirringstirred at room temperature overnight
  4. washthe organic phase was washed with water
  5. dry with materialAfter the organic solution was dried over anhydrous sodium sulfate
  6. filtrationthe organic phase was filtered
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-669f2a69a2994bd391a10f5387607fdf
Source dataset
uspto-grants-2005_01
Patent number
US06844429B2

Reaction notes

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