Cesium carbonate → HCID 86761140, compound

HRID 2355132Notes

Reaction equation

HRID 2355132 reaction equation
[CH2:1]([C:8]1[O:9][C:10]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([OH:23])[CH:17]=[CH:16]3)=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[Cs+].[Cs+]>CC(C)=O>[CH2:1]([C:8]1[O:9][C:10]([C:13]2[CH:14]=[C:15]3[C:20](=[CH:21][CH:22]=2)[CH:19]=[C:18]([O:23][CH2:25][C:26]([O:28][CH3:29])=[O:27])[CH:17]=[CH:16]3)=[CH:11][N:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 60984Methyl bromoacetateHCID 68451974HCID 68451974, compound

Product 1

HCID 86761140HCID 86761140, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-(2-benzyl-1,3-oxazol-5-yl)-2-naphthol (500 mg, 1.66 mmol), prepared in step 3 of Example 11, methyl bromoacetate (160 μL, 1.69 mmol) and cesium carbonate (1.08 g, 3.32 mmol) in 45 mL of acetone was stirred under nitrogen at room temperature for 16 h (overnight). The acetone was removed under reduced pressure and the residue partitioned between methylene chloride and water. The organic layer was separated and the aqueous layer extracted two times with methylene chloride. The combined extracts were dried (MgSO4), filtered and the solvent removed under reduced pressure to produce 628 mg of a white solid. Purification of the solid on a Biotage KP-SIL 60 Å 25+M 40 g column using methylene chloride-ethyl acetate as the eluent gave methyl {[6-(2-benzyl-1,3-oxazol-5-yl)-2-naphthyl]oxy} acetate (454 mg, 73%) as a white solid, mp 140-142° C. Elemental Analysis for C23H19NO4 Calc'd: C, 73.98; H, 5.13; N, 3.75. Found: C, 73.49; H, 4.96; N, 3.45.

Workup

  1. customThe acetone was removed under reduced pressure
  2. customthe residue partitioned between methylene chloride and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted two times with methylene chloride
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-224f70b2139843f397b96c35c88e2305
Source dataset
uspto-grants-2010_07
Patent number
US07754747B2

Reaction notes

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