Potassium Carbonate → HCID 23552109, compound

HRID 1994076Notes

Reaction equation

HRID 1994076 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:20][C:21]2[N:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[O:24][C:25]=2[CH3:26])[CH:6]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 39129Methyl 3-HydroxyphenylacetateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 23552109HCID 23552109, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a stirred solution of (3-hydroxy-phenyl)-acetic acid methyl ester (4.26 g, 25.66 mmol) and potassium carbonate (7.1 g, 51.33 mmol) in DMF (60 mL) is added 4-chloromethyl-5-methyl-2-phenyl-oxazole (5.33 g, 25.66 mmol) at RT. The reaction mixture is stirred for 16 h at 40° C. followed by 16 h at 60° C. The reaction mixture is cooled to RT, diluted with ethyl acetate, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated at reduced pressure. The crude product is purified on a Biotage 40M column using 25% ethyl acetate in hexane to yield [3-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-phenyl]-acetic acid methyl ester as a white solid.

Workup

  1. waitfollowed by 16 h at 60° C
  2. temperatureThe reaction mixture is cooled to RT
  3. washwashed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customThe crude product is purified on a Biotage 40M column

Sources & evidence

ORD record
ord-2223d179f3c744d98a6ecb6be8bd8aeb
Source dataset
uspto-grants-2010_01
Patent number
US07652061B2

Reaction notes

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