Potassium Iodide → HCID 10342370, compound

HRID 257635Notes

Reaction equation

HRID 257635 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]=[C:8]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]([OH:24])[CH:21]=[CH:22][CH:23]=3)[O:9][C:10]=2[C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[CH:2]1.Br[CH2:26][C:27]([O:29][CH3:30])=[O:28].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[S:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:7]=[C:8]([CH2:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:21]=[CH:22][CH:23]=3)[O:24][CH2:26][C:27]([O:29][CH3:30])=[O:28])[O:9][C:10]=2[C:11]2[CH:15]=[CH:14][S:13][CH:12]=2)=[CH:2]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19783604HCID 19783604, compound

Product 1

HCID 10342370HCID 10342370, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-[2-[4,5-di(3-thienyl)-2-oxazolyl]ethyl]phenol (2.00 g, 5.6 mmol), methyl bromoacetate (1.04 g, 6.8 mmol), potassium carbonate (0.94 g, 6.8 mmol), potassium iodide (catalytic amount) and acetonitrile (100 mL) was stirred at reflux under an atmosphere of nitrogen. After 15 hours, the mixture was cooled, filtered and concentrated and the residue subjected to chromatography on a column of silica gel. Elution with a mixture of hexanes and ethyl acetate (7:2) gave methyl [3-[2-[4,5-di(3-thienyl)-2-oxazolyl]ethyl]phenoxy]acetate (1.95 g, 80%) as an oil.

Workup

  1. temperatureat reflux under an atmosphere of nitrogen
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washElution
  6. additionwith a mixture of hexanes and ethyl acetate (7:2)

Sources & evidence

ORD record
ord-5ae716a4b760492a94777c6e77578ecc
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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