Potassium Iodide → Methyl 2-[4-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetate

HRID 257621Notes

Reaction equation

HRID 257621 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[C:1]1([C:7]2[N:8]=[C:9]([CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:25]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 197836234-[2-(4,5-Diphenyl-2-oxazolyl)ethyl]phenol

Product 1

HCID 19783610Methyl 2-[4-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetateYield 103.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenol (6.00 g, 17 mmol), methyl bromoacetate (2.96 g, 1.83 mL, 19 mmol), potassium carbonate (2.91 g, 21 mmol), potassium iodide (catalyic amount) and acetonitrile (80 mL) was stirred at reflux. After 1 hour, the mixture was cooled, filtered and the solvent removed to leave a crystalline solid that was tritrated with hexanes and filtered to give methyl 2-[4-[2-(4,5-diphenyl-2-oxazolyl)ethyl]phenoxy]acetate (7.27 g, 100%). An analytical sample was obtained by recrystallizing a 2.25 g batch from methanol to give 1.70 g of pure material which had m.p. 122°-125° C.

Workup

  1. temperatureat reflux
  2. temperaturethe mixture was cooled
  3. filtrationfiltered
  4. customthe solvent removed
  5. customto leave a crystalline solid
  6. filtrationfiltered

Sources & evidence

ORD record
ord-cb225e502ee2476fbaffafdc65639310
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Reaction notes

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