Tetrahydrofuran → (2-Chloropyridin-4-yl)methanol
Reaction equation
O1CCCC1.[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][N:15]=1)[C:10](O)=[O:11]>C(OCC)(=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:13]=[CH:14][N:15]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Borane-dimethyl sulfide complex (14.30 mL, 14.30 mmols) was added to tetrahydrofuran solution of 2-chloroisonicotinic acid (17.56 g, 11.5 mmols) under cooling with ice, and stirred at room temperature for 2.5 days, followed by further an hour's stirring at 50° C. Cooling the reaction liquid to room temperature, ethyl acetate was added, followed by washing with saturated aqueous ammonium chloride solution and saturated brine and drying over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the tide compound (15.0 g, 93%) was obtained.
Workup
- temperatureunder cooling with ice
- waitfollowed by further an hour
- stirring's stirring at 50° C
- temperatureCooling
- customthe reaction liquid to room temperature
- washby washing with saturated aqueous ammonium chloride solution and saturated brine
- dry with materialdrying over anhydrous sodium sulfate
- concentrationConcentrating the solvent under reduced pressure
Sources & evidence
- ORD record
- ord-3fa492606d864acd8a6b58ac8a2f15f7
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07732456B2
Reaction notes
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