Methanol → 5-Fluoro-6-methyl-3-pyridinecarboxaldehyde
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[N:6][C:7]=1[CH3:8].CO>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[O:10])[CH:5]=[N:6][C:7]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 35 °C
Procedure
To a solution of (5-fluoro-6-methyl-3-pyridinyl)methanol (468 mg, 3.32 mmol) in DCM (4 ml) was added CrO2 (Magtrieve) (4.2 g, 49.7 mmol). The mixture was stirred at 35° C. for 4 h. TLC (5% MeOH in DCM) showed starting material remaining. An excess of CrO2 (Magtrieve) (2.8 g, 33.3 mmol) was added. The mixture was stirred at 35° C. for 48 h. The solids were filtered off and the solvent evaporated to afford 144 mg (28%) of the title compound.
Workup
- stirringThe mixture was stirred at 35° C. for 48 h
- filtrationThe solids were filtered off
- customthe solvent evaporated
Sources & evidence
- ORD record
- ord-a7d822c0cf9941ffb7105f0ac8ea2178
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097628B2
Reaction notes
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