Sodium Carbonate → 5-Methyl-2-phenyloxazole

HRID 915666Notes

Reaction equation

HRID 915666 reaction equation
O=[C:2]([CH3:13])[CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C([O-])([O-])=O.[Na+].[Na+]>OS(O)(=O)=O>[CH3:13][C:2]1[O:12][C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 569897N-(2-Oxopropyl)benzamide

Product 1

HCID 2478295-Methyl-2-phenyloxazoleYield 88%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Heat a solution of N-(2-oxopropyl)benzamide (1.0 g, 5.65 mmol) in concentrated H2SO4 (10 mL) at 100° C. for 1 hour. Cool the reaction, pour over ice, neutralize with solid Na2CO3, and extract with ethyl acetate (200 mL). Wash the organic phase with brine (75 mL), dry (Na2SO4), filter, and concentrate to afford a yellow oil. Perform flash chromatography on silica gel, eluting with 100% ethyl acetate, to afford 790 mg (88% yield) of 5-methyl-2-phenyloxazole. MS: m/e=160 (MH+)

Workup

  1. temperatureCool
  2. customthe reaction
  3. additionpour over ice
  4. extractionextract with ethyl acetate (200 mL)
  5. washWash the organic phase with brine (75 mL)
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate
  9. customto afford a yellow oil
  10. washPerform flash chromatography on silica gel, eluting with 100% ethyl acetate

Sources & evidence

ORD record
ord-e899f35840144dd68242406086f80853
Source dataset
uspto-grants-2007_09
Patent number
US07265246B2

Reaction notes

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