Dimethylformamide → HCID 59296124, compound

HRID 2233558Notes

Reaction equation

HRID 2233558 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:19]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[O:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:19][OH:24])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 59296122HCID 59296122, compound

Product 1

HCID 59296124HCID 59296124, compound

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 57417360Sodium chloride; waterSolvent

Procedure

30.7 g of crude 4-Bromomethyl-2-(4-methoxy-phenyl)-oxazole-5-carboxylic acid ethyl ester were dissolved in 170 ml dry dimethylformamide. 29.95 g Silver trifluoroacetate were added and the mixture was stirred at room temperature overnight. 100 ml brine were added and the mixture was stirred for one hour. 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 1 n-heptane:ethyl acetate=5:1=>ethylacetate) to obtain 17.8 g 4-Hydroxymethyl-2-(4-methoxy-phenyl)-oxazole-5-carboxylic acid ethyl ester as a solid.

Workup

  1. stirringthe mixture was stirred for one hour
  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 1 n-heptane:ethyl acetate=5:1=>ethylacetate)

Sources & evidence

ORD record
ord-1f8e6cc34e2a471988a66242ea07f832
Source dataset
uspto-grants-2010_05
Patent number
US07709509B2

Reaction notes

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