Ethanol → 4-(1,3-Oxazol-2-YL)benzaldehyde
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.BrN1C(=[O:19])CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C(O)C>C(Cl)(Cl)(Cl)Cl.[N+]([O-])([O-])=O.[Ag+]>[O:9]1[CH:10]=[CH:11][N:12]=[C:8]1[C:5]1[CH:4]=[CH:3][C:2]([CH:1]=[O:19])=[CH:7][CH:6]=1Participants
7
Conditions
- Temperature
- 100 °C
Procedure
To 2-(4-methylphenyl)oxazole (6.41 g, 40.3 mmol) and N-bromosuccinimide (14.7 g, 82.6 mmol) in carbon tetrachloride (300 mL) was added 2,2′-azobisisobutyronitrile (500 mg, 3.1 mmol) and the reaction mixture was heated at 100° C. for 12 h. The reaction mixture was cooled to 0° C., filtered through a fritted funnel, and concentrated in vacuo. To this crude reaction mixture was added 95% ethanol (300 mL) and silver nitrate (15.1 g, 88.8 mmol), and the reaction mixture was refluxed for 4 h, cooled to room temperature, filtered through a fritted funnel, and concentrated in vacuo. Purification by medium pressure liquid chromatography (SiO2, 10:1 hexanes/ethyl acetate) gave 880 mg (13%, 2 steps) of the title compound. MS 174 (M+H)+.
Workup
- temperatureThe reaction mixture was cooled to 0° C.
- filtrationfiltered through a fritted funnel
- concentrationconcentrated in vacuo
- customTo this crude reaction mixture
- temperaturethe reaction mixture was refluxed for 4 h
- temperaturecooled to room temperature
- filtrationfiltered through a fritted funnel
- concentrationconcentrated in vacuo
- customPurification by medium pressure liquid chromatography (SiO2, 10:1 hexanes/ethyl acetate)
Sources & evidence
- ORD record
- ord-4638b55c7c064300a8f067e14dc66fb3
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825170B2
Reaction notes
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