Acetone → 2-fluoro-4-formyl-N-methylbenzamide
Reaction equation
[F:1][C:2]1[CH:11]=[C:10]([CH:12]=C)[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5].CC(C)=[O:16].C(#N)C.I([O-])(=O)(=O)=O.[Na+]>[Os]=O.O>[F:1][C:2]1[CH:11]=[C:10]([CH:12]=[O:16])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][CH3:7])=[O:5]Participants
Procedure
To a solution of 2-fluoro-N-methyl-4-vinylbenzamide (0.62 g) in a mixed solvent of acetone (23 mL)-acetonitrile (23 mL)-water (23 mL) were added osmium oxide (fixed catalyst I) (0.44 g) and sodium periodate (3.69 g), and the mixture was stirred overnight at room temperature. The insoluble substance was removed by filtration, and the filtrate was diluted with ethyl acetate and water. The insoluble substance was removed by filtration, the filtrate was concentrated under reduced pressure, and the residue was diluted with ethyl acetate. The mixture was washed with water and saturated brine, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was subjected to short silica gel column chromatography, and the solvent was evaporated under reduced pressure to give the title compound (0.62 g).
Workup
- customThe insoluble substance was removed by filtration
- additionthe filtrate was diluted with ethyl acetate and water
- customThe insoluble substance was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- additionthe residue was diluted with ethyl acetate
- washThe mixture was washed with water and saturated brine
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- customthe solvent was evaporated under reduced pressure
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-b45a042cf3c245c694e6495dfc4524c3
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315458B2
Reaction notes
Loading…