Ethylene Glycol → HCID 86748385, compound

HRID 1769242Notes

Reaction equation

HRID 1769242 reaction equation
[Br:1][C:2]1[C:3](=[O:10])[C@@H:4]2[O:9][CH2:8][C@H:6]([CH:7]=1)[O:5]2.[CH2:11](O)[CH2:12][OH:13].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C>C1C=CC=CC=1>[CH2:12]1[O:13][C:3]2([C:2]([Br:1])=[CH:7][C@H:6]3[CH2:8][O:9][C@@H:4]2[O:5]3)[O:10][CH2:11]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 11458381HCID 11458381, compound

Product 1

HCID 86748385HCID 86748385, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

22 g of 1,6-anhydro-3-bromo-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose was dissolved in 500 ml of dry benzene, and 66 g of ethylene glycol and 3 g of p-toluenesulfonic acid monohydrate were added thereto. The mixture was refluxed under heating while removing formed water. 19 hours later, disappearance of the starting material was confirmed by TLC, and the reaction mixture was cooled to room temperature. Then, 500 ml of ethyl acetate was added thereto, and the mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The obtained crude crystals were purified by silica gel column chromatography (ethyl acetate: hexane=1:1) to obtain 20 g of 1,6-anhydro-3-bromo-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose ethylene acetal as white crystals. The NMR analytical data of this product are as follows.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating
  3. customwhile removing
  4. customformed water
  5. custom19 hours
  6. washthe mixture was washed three times with 200 ml of a saturated sodium chloride aqueous solution
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe obtained crude crystals
  10. customwere purified by silica gel column chromatography (ethyl acetate: hexane=1:1)

Sources & evidence

ORD record
ord-d8b6c53117784831bce26aa5044fb5a5
Source dataset
uspto-grants-1995_01
Patent number
US05380834

Reaction notes

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