Sodium borohydride → 2-Fluoro-3-(hydroxymethyl)pyridine
Reaction equation
[F:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[BH4-].[Na+]>C(O)C>[F:1][C:2]1[C:7]([CH2:8][OH:9])=[CH:6][CH:5]=[CH:4][N:3]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
In a 250 mL round bottom flask, 2-fluoropyridine-3-carbaldehyde (2.5 g, 20 mmol) was dissolved in anhydrous ethanol (20 mL). The solution was cooled to 0° C. under nitrogen. NaBH4 (1.5 g, 40 mmol) was added in one portion. The mixture was stirred at room temperature for 2 hours and quenched by addition of water (5 mL). Na2SO4 (20 g) was added. After 10 minutes, the mixture was filtered. The filtrate was evaporated to provide (2-fluoropyridin-3-yl)methanol.
Workup
- customquenched by addition of water (5 mL)
- additionNa2SO4 (20 g) was added
- waitAfter 10 minutes
- filtrationthe mixture was filtered
- customThe filtrate was evaporated
Sources & evidence
- ORD record
- ord-4647fe67ee744438ac10db5bcb262e57
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315521B2
Reaction notes
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