2-Bromomethyl-4,5-diphenyl-oxazole → Methyl 3-[3-[(4,5-diphenyl-2-oxazolyl)-methoxy]phenyl]propanoate

HRID 257628

Reaction equation

HRID 257628 reaction equation
Br[CH2:2][C:3]1[O:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[OH:20][C:21]1[CH:22]=[C:23]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:24]=[CH:25][CH:26]=1>>[C:8]1([C:6]2[N:7]=[C:3]([CH2:2][O:20][C:21]3[CH:22]=[C:23]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[CH:24]=[CH:25][CH:26]=3)[O:4][C:5]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 5685992-Bromomethyl-4,5-diphenyl-oxazoleHCID 1512675Methyl 3-(3-hydroxyphenyl)propionate

Product 1

HCID 10070328Methyl 3-[3-[(4,5-diphenyl-2-oxazolyl)-methoxy]phenyl]propanoateYield 833.6%

Procedure

A mixture of 2-bromomethyl-4,5-diphenyloxazole (10.00 g, 3 mmol), methyl 3-(3-hydroxyphenyl)propanoate (5.73 g, 3 mmol) potassium carbonate (4.83 g, 3.5 mmol) potassium iodide (catalytic amount) and acetonetrile (150 mL) was stirred at reflux temperature. After 30 minutes, the mixture was filtered, concentrated in vacuo and the residual oil chromatographed on a column of silica gel. Elution with a mixture of hexanes and diethyl ether (3:1) furnished methyl 3-[3-((4,5-diphenyl-2-oxazolyl)methoxy]phenyl]propanoate (10.34 g, 78%) as an oil. An analytical sample was prepared by subjecting a 4 g sample to chromatography under the conditions described above to furnish pure material as an oil.

Workup

  1. temperatureat reflux temperature
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customthe residual oil chromatographed on a column of silica gel
  5. washElution
  6. additionwith a mixture of hexanes and diethyl ether (3:1)

Sources & evidence

ORD record
ord-e370f361ed2a458c9049b70c3aca86eb
Source dataset
uspto-grants-1993_11
Patent number
US05262540

Linked notes

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