Hydrochloric Acid → 1,2-Ethanediol, 1-phenyl-, 2-methanesulfonate, (1R)-

HRID 478999Notes

Reaction equation

HRID 478999 reaction equation
[CH3:1][S:2]([O:5][CH2:6][C@@H:7]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[O:8]C1CCCCO1)(=[O:4])=[O:3].Cl>CO>[CH3:1][S:2]([O:5][CH2:6][C@H:7]([OH:8])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 9922367HCID 9922367, compound

Product 1

HCID 113104631,2-Ethanediol, 1-phenyl-, 2-methanesulfonate, (1R)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into methanol (10 ml) were added (R)-2-phenyl-2-(3,4,5,6-tetrahydro-[2H]-pyran-2-yloxy)ethyl methanesulfonate (2.0 g) and hydrochloric acid (0.07 g), and the resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was neutralized, concentrated, and then ethyl acetate and water were added to the resulting residue. The organic layer was collected by layer separation, washed with a saturated aqueous sodium chloride solution and dried with anhydrous magnesium sulfate. The desiccant was filtered off and then the solvent was distilled off to obtain a colorless oily compound mentioned above (1.4 g, 97.2%).

Workup

  1. concentrationconcentrated
  2. additionethyl acetate and water were added to the resulting residue
  3. customThe organic layer was collected by layer separation
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationThe desiccant was filtered off
  7. distillationthe solvent was distilled off
  8. customto obtain a colorless oily compound

Sources & evidence

ORD record
ord-ada5fb773f29489681f7fa33547a2e3d
Source dataset
uspto-grants-2003_11
Patent number
US06642395B1

Reaction notes

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