Ethanol → (3-Chloropyridin-4-yl)methanol
Reaction equation
[Cl:1][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(O)C.[BH4-].[Na+]>[Cl-].[Na+].O>[Cl:1][C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 1.53 g of 3-chloroisonicotinaldehyde and 5 ml of ethanol was gradually added 0.40 g of sodium borohydride under ice-cooling, and the mixture was stirred under ice-cooling for 1 hour, and subsequently at room temperature for 1 hour. Saturated brine was added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layers were combined and dried over magnesium sulfate. The resulting mixture was concentrated under reduced pressure to obtain 1.40 g of (3-chloropyridin-4-yl)methanol.
Workup
- temperaturecooling
- temperaturecooling for 1 hour
- extractionthe mixture was extracted twice with ethyl acetate
- dry with materialdried over magnesium sulfate
- concentrationThe resulting mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-1cfaa679637c436e9665911fc57648dd
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796306B2
Reaction notes
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