Dimethyl Sulfate → 6-Methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde
Reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[CH:12]=[O:13].[C:14]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:14][O:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6]([CH3:9])=[N:7][O:8][C:4]=2[C:3]=1[CH:12]=[O:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 6-hydroxy-3-methylbenzo[d]isoxazole-7-carbaldehyde (437 mg; 2.46 mmol) and K2CO3 (409 mg; 2.96 mmol) in anh. acetone (21 ml) was treated with dimethyl sulfate (373 mg; 2.96 mmol), and the resulting mixture was heated to 60° C., under nitrogen, for 1.5 h. After cooling to rt, the resulting reaction mixture was filtered, and the filtrate was concentrated to dryness under reduced pressure. DCM was added, and the mixture was washed successively with 1 M aq. NH4OH, water, and brine. The organic layer was dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure to give 6-methoxy-3-methylbenzo[d]isoxazole-7-carbaldehyde as an orange solid. LC-MS (conditions A): tR=0.53 min.; [M+H]+: 192.12 g/mol.
Workup
- temperatureAfter cooling to rt
- customthe resulting reaction mixture
- filtrationwas filtered
- concentrationthe filtrate was concentrated to dryness under reduced pressure
- additionDCM was added
- washthe mixture was washed successively with 1 M aq. NH4OH, water, and brine
- dry with materialThe organic layer was dried over anh. MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-95a078c0dae040f5a93edf9049dc5f11
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242970B2
Reaction notes
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