Potassium Carbonate → 4-Methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-benzoic acid methyl ester

HRID 644011Notes

Reaction equation

HRID 644011 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[C:6](=[CH:11][CH:12]=1)[C:7]([O:9][CH3:10])=[O:8].Br[CH2:15][C:16]1[CH:36]=[CH:35][C:19]([O:20][CH2:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:10][O:9][C:7](=[O:8])[C:6]1[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][C:5]=1[O:13][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:20][CH2:21][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79523Methyl 4-methoxysalicylateHCID 685793194-[2-(4-Bromomethyl-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazole

Product 1

HCID 587911484-Methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 4-methoxysalicylate (176 mg, 0.97 mmol), the title C compound, 4-[2-(4-bromomethyl-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazole (300 mg, 0.81 mmol) and potassium carbonate (334 mg, 2.42 mmol) in DMF (10 mL) is stirred at RT overnight. The mixture is partitioned between EtOAc and water. The organic phase is washed with brine, dried over magnesium sulfate, and concentrated. The residue is chromatographed on silica gel using 15% EtOAc in hexane as the eluent to give 4-methoxy-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}-benzoic acid methyl ester.

Workup

  1. customThe mixture is partitioned between EtOAc and water
  2. washThe organic phase is washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on silica gel using 15% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-77df28e835254c93befeaeef0b4cd768
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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