Potassium Carbonate → 2-Methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}4-propoxy-benzoic acid allyl ester

HRID 644014Notes

Reaction equation

HRID 644014 reaction equation
[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:11]([CH3:12])=[CH:10][C:9]([O:13][CH2:14][CH2:15][CH3:16])=[CH:8][C:7]=1[OH:17])[CH:2]=[CH2:3].Br[CH2:20][C:21]1[CH:41]=[CH:40][C:24]([O:25][CH2:26][CH2:27][C:28]2[N:29]=[C:30]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[O:31][C:32]=2[CH3:33])=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:4][C:5](=[O:18])[C:6]1[C:7]([O:17][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:25][CH2:26][CH2:27][C:28]3[N:29]=[C:30]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[O:31][C:32]=3[CH3:33])=[CH:40][CH:41]=2)=[CH:8][C:9]([O:13][CH2:14][CH2:15][CH3:16])=[CH:10][C:11]=1[CH3:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 685793194-[2-(4-Bromomethyl-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazoleHCID 685797952-Hydroxy-6-methyl-4-propoxy-benzoic acid allyl ester

Product 1

HCID 685796982-Methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}4-propoxy-benzoic acid allyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the title C compound, 2-hydroxy-6-methyl-4-propoxy-benzoic acid allyl ester (400 mg, 1.6 mmol), the title C compound in Example 11, 4-[2-(4-bromomethyl-phenoxy)-ethyl]-5-methyl-2-phenyl-oxazole (595 mg, 1.6 mmol) and potassium carbonate (662 mg, 4.79 mmol) in 15 mL of DMF 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 under vacuum. The residue is chromatographed on silica gel using 15% EtOAc in hexane as the eluent to obtain 2-methyl-6-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzyloxy}4-propoxy-benzoic acid allyl ester as an oil: ESI-MS 542 [M+1]+.

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 under vacuum
  5. customThe residue is chromatographed on silica gel using 15% EtOAc in hexane as the eluent

Sources & evidence

ORD record
ord-b344a7839aed4b1587856d034e63411e
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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