Water → 1,3-Benzoxazole-2-carbaldehyde
Reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=C/N(C)C.O.CC[O:18]C(C)=O>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]=[O:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To (E)-2-(benzo[d]oxazol-2-yl)-N,N-dimethylethenamine (1 g, 5.32 mmol) in THF (15 mL) at 0° C. was added water (15 mL) and NaIO4 (3.4 g, 16 mmol). The resulting mixture was stirred at 0° C. for 10 min, then at room temperature for 2 h. To the solution was added H2O and EtOAc and then the mixture was filtered. The clear solution was extracted with EtOAc and the organic phase was washed with aqueous NaHCO3 solution. The organic phase was concentrated and the residue was purified by column chromatography to give the title compound (120 mg). MS (ESI) m/z 148 (M+H+).
Workup
- waitat room temperature for 2 h
- filtrationthe mixture was filtered
- extractionThe clear solution was extracted with EtOAc
- washthe organic phase was washed with aqueous NaHCO3 solution
- concentrationThe organic phase was concentrated
- customthe residue was purified by column chromatography
Sources & evidence
- ORD record
- ord-605ba309bf5647b7a7231e7cfb5ee0d1
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969349B2
Reaction notes
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