Ethyl Acetate → 2-Methyl-6-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzyloxy]-4-propoxy-benzoic acid methyl ester

HRID 644007Notes

Reaction equation

HRID 644007 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:6][C:5]=1[OH:15].Br[CH2:18][C:19]1[CH:38]=[CH:37][C:22]([O:23][CH2:24][C:25]2[N:26]=[C:27]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[O:28][C:29]=2[CH3:30])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>CN(C=O)C.CCCCCC>[CH3:1][O:2][C:3](=[O:16])[C:4]1[C:5]([O:15][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:23][CH2:24][C:25]3[N:26]=[C:27]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[O:28][C:29]=3[CH3:30])=[CH:37][CH:38]=2)=[CH:6][C:7]([O:11][CH2:12][CH2:13][CH3:14])=[CH:8][C:9]=1[CH3:10]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 685799434-(4-Bromomethyl-phenoxymethyl)-5-methyl-2-phenyl-oxazoleHCID 685799482-Hydroxy-6-methyl-4-propoxy-benzoic acid methyl ester

Product 1

HCID 592632962-Methyl-6-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzyloxy]-4-propoxy-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

A mixture of the title A compound, 2-hydroxy-6-methyl-4-propoxy-benzoic acid methyl ester (407 mg, 1.81 mmol), the title D compound, 4-(4-bromomethyl-phenoxymethyl)-5-methyl-2-phenyl-oxazole (650 mg, 1.81 mmol) and potassium carbonate (751 mg, 5.44 mmol) in DMF is stirred at RT overnight. The mixture is then partitioned between EtOAc and water. The organic layer is washed with brine, dried with magnesium sulfate and concentrated under vacuum to give the crude product. Chromatography on silica gel, using 10% EtOAc in hexane gives 2-methyl-6-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzyloxy]-4-propoxy-benzoic acid methyl ester as a white foam: ESI-MS 502 [M+1]+.

Workup

  1. customThe mixture is then partitioned between EtOAc and water
  2. washThe organic layer is washed with brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give the crude product

Sources & evidence

ORD record
ord-63c4b3974bdc4ebb827541f4c57dc3a4
Source dataset
uspto-grants-2010_04
Patent number
US07700637B2

Reaction notes

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