Dimethylformamide → 5-Hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester

HRID 2233564Notes

Reaction equation

HRID 2233564 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[O:9][C:10]=1[CH2:11]Br)=[O:5])[CH3:2].CN(C)C=[O:24]>[Cl-].[Na+].O.FC(F)(F)C([O-])=O.[Ag+]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[O:9][C:10]=1[CH2:11][OH:24])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 592961295-Bromomethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester

Product 1

HCID 592962005-Hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

8.0 g 5-Bromomethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester were dissolved in 50 ml dry dimethylformamide. 7.8 g Silver trifluoroacetate were added and the mixture was stirred at room temperature for two hours. 30 ml brine were added and the mixture was stirred for two hours. The reaction mixture was filtered through a pad of celite, the solvent removed in vacuo and the resulting residue dissolved in 200 ml ethanol. The mixture was heated to reflux for three hours. Then the solvent was removed in vacuo and the residue dissolved in water and extracted five times with ethyl acetate. The combined organic layers were dried over MgSO4, the solvent removed in vacuo and the residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=2:3=>ethylacetate) to obtain 4.8 g 5-hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-4-carboxylic acid ethyl ester as a solid.

Workup

  1. stirringthe mixture was stirred for two hours
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customthe solvent removed in vacuo
  4. dissolutionthe resulting residue dissolved in 200 ml ethanol
  5. temperatureThe mixture was heated
  6. temperatureto reflux for three hours
  7. customThen the solvent was removed in vacuo
  8. dissolutionthe residue dissolved in water
  9. extractionextracted five times with ethyl acetate
  10. dry with materialThe combined organic layers were dried over MgSO4
  11. customthe solvent removed in vacuo
  12. customthe residue purified by flash chromatography on silica gel (eluting with n-heptane:ethyl acetate=2:3=>ethylacetate)

Sources & evidence

ORD record
ord-f32d0050c15e465987efab92c967f4c0
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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