Potassium Carbonate → HCID 86603518, compound

HRID 2355116Notes

Reaction equation

HRID 2355116 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:29]=[CH:28][CH:27]=[CH:26][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([OH:25])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4].Br[CH2:31][C:32]([O:34][CH3:35])=[O:33].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([C:5]1[O:6][C:7]2[CH:29]=[CH:28][CH:27]=[CH:26][C:8]=2[C:9]=1[C:10]1[O:11][C:12]([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20]([O:25][CH2:31][C:32]([O:34][CH3:35])=[O:33])[CH:19]=[CH:18]3)=[CH:13][N:14]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 68452159HCID 68452159, compound

Product 1

HCID 86603518HCID 86603518, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthol (306 mg, 0.792 mmol), prepare in step 5 of Example 2, methyl bromoacetate (75 μL, 0.792 mmol) and potassium carbonate (556 mg, 4.02 mmol) in 35 mL of DMF was stirred under nitrogen at room temperature for 19 h (overnight). The reaction was partitioned between ethyl acetate and water. The organic layer was separated and extracted three times with water. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to give methyl ({6-[2-(2-butyl-1-benzofuran-3-yl)-1,3-oxazol-5-yl]-2-naphthyl}oxy)acetate (364 mg, 96%) as a yellow solid, mp 149-151° C. Elemental Analysis for C28H25NO5 Calc'd: C, 73.83; H, 5.53; N, 3.07. Found: C, 73.55; H, 5.72; N, 3.08.

Workup

  1. customThe reaction was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionextracted three times with water
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-49497e064e8347178c4f45f3e8608b4f
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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