Triethylamine → HCID 67086796, compound

HRID 2365483Notes

Reaction equation

HRID 2365483 reaction equation
[CH2:1]1[O:3][C@H:2]1[CH2:4][OH:5].[I:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.C(N(CC)CC)C>C(O)C>[I:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:1][C@@H:2]([OH:3])[CH2:4][OH:5])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108944-IodophenolHCID 6973630(-)-Glycidol

Product 1

HCID 67086796HCID 67086796, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(S)-Glycidol (0.36 ml, 5.5 mmol) is added to a solution of 4-iodophenol (1 g, 4.5 mmol) and triethylamine (31 ml, 0.2 mmol) in ethanol (5 ml) and the resulting light brown solution is heated at reflux for 15 hours. The reaction is allowed to cool to room temperature and the solvent removed in vacuo. The residue is purified by chromatography (SiO2, EtOAc/iso-hexane) to afford (S)-3-(4-Iodo-phenoxy)-propane-1,2-diol as a colourless oil.

Workup

  1. temperaturethe resulting light brown solution is heated
  2. temperatureat reflux for 15 hours
  3. customthe solvent removed in vacuo
  4. customThe residue is purified by chromatography (SiO2, EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-f7177079cf5e4ec9adf88b9cf73769e1
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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