Water → 4-Phenyl-1,3-oxazole

HRID 2399913Notes

Reaction equation

HRID 2399913 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH:11]([O-:13])=O.[NH4+:14].O>C(O)=O>[C:5]1([C:3]2[N:14]=[CH:11][O:13][CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6259Phenacyl bromideHCID 2723923Ammonium formate

Product 1

HCID 5892794-Phenyl-1,3-oxazoleYield 31%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 2-bromoacetophenone and ammonium formate in formic acid was stirred at reflux under nitrogen for 2 hours. The cooled reaction mixture was treated with 400 mL of H2O and extracted with ether (3×200 mL). The combined organics were washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (eluting with EtOAc/hexanes, 1:9) to afford 8.9 g (31%) of 4-phenyloxazole as a yellow oil.

Workup

  1. temperatureat reflux under nitrogen for 2 hours
  2. customThe cooled reaction mixture
  3. extractionextracted with ether (3×200 mL)
  4. washThe combined organics were washed with saturated aqueous NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography (eluting with EtOAc/hexanes, 1:9)

Sources & evidence

ORD record
ord-d210e6dcc0614ccab50e24bcaaf1dcbc
Source dataset
uspto-grants-1995_09
Patent number
US05451686

Reaction notes

Loading…