Sodium borohydride → 1-(3-(Trifluoromethyl)pyridin-2-yl)ethanol
Reaction equation
[C:1]([C:4]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][N:5]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO>[F:13][C:10]([F:11])([F:12])[C:9]1[C:4]([CH:1]([OH:3])[CH3:2])=[N:5][CH:6]=[CH:7][CH:8]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
Dissolve 2-acetyl-3-trifluoromethylpyridine (76 g, 0.4021 moles) in anhydrous MeOH (1100 mL) and cool the resulting solution at −10° C. under N2 atmosphere. Add NaBH4 (16.0 g, 0.4238 moles) in small portions over a period of 45 minutes and stir further at −10° C. for an additional 45 minutes. Quench the reaction mixture with water (100 mL) and warm to room temperature. Concentrate the reaction mixture under vacuum, dilute with water (500 mL), extract with EtOAc (3×250 mL) and dry (MgSO4). Filter and concentrate the dried extract under vacuum to afford the title product as a yellow oil.
Workup
- customQuench the reaction mixture with water (100 mL)
- temperaturewarm to room temperature
- concentrationConcentrate the reaction mixture under vacuum
- additiondilute with water (500 mL)
- extractionextract with EtOAc (3×250 mL)
- dry with materialdry (MgSO4)
- filtrationFilter
- concentrationconcentrate the dried
- extractionextract under vacuum
Sources & evidence
- ORD record
- ord-9eb8b6bd06674c6998079d27854771e2
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07935702B2
Reaction notes
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