Potassium Carbonate → 4-[2-Oxazol-2-yl-5-(thiophen-3-ylmethoxy)-phenoxy]-4-o-tolyl-butyric acid

HRID 322899Notes

Reaction equation

HRID 322899 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[CH:24][C:7]=1[O:8][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:10][CH2:11][C:12]([O:14]CC)=[O:13].C(=O)([O-])[O-].[K+].[K+]>CO>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][C:30]2[CH:34]=[CH:33][S:32][CH:31]=2)=[CH:24][C:7]=1[O:8][CH:9]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[CH3:23])[CH2:10][CH2:11][C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 54203548HCID 54203548, compound

Product 1

HCID 106948044-[2-Oxazol-2-yl-5-(thiophen-3-ylmethoxy)-phenoxy]-4-o-tolyl-butyric acidYield 53.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of ethyl (RS)-4-[2-(oxazol-2-yl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoate (140 mg) in methanol (25 mL) containing 10% w/v potassium carbonate (2 mL) is stirred at reflux for 2 hours. The reaction mixture is partitioned between 1 N HCl (50 mL) and ethyl acetate (50 mL) then the organic phase is washed with water (2×50 mL), dried over magnesium sulphate, filtered and concentrated under reduced pressure. Recrystallisation from cyclohexane/ethyl acetate gives (RS)-4-[2-(oxazol-2-yl)-5-(3-thienylmethoxy)phenoxy]-4-(2-methylphenyl)butanoic acid as a white solid (70 mg), m.p. 112-114° C. [Elemental analysis:- C,66.8, H, 5.16, N, 3.12%. Calculated:- C,66.5, H, 5.04, N, 3.01%]

Workup

  1. temperatureat reflux for 2 hours
  2. customThe reaction mixture is partitioned between 1 N HCl (50 mL) and ethyl acetate (50 mL)
  3. washthe organic phase is washed with water (2×50 mL)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallisation from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-d60fda16019f4d1583fd6fb2661541f1
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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