Diisobutylaluminum hydride → (5-Chloro-6-(difluoromethoxy)pyridin-3-yl)methanol
Reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH:13]([F:15])[F:14])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C[AlH]CC(C)C)C.[OH-].[Na+].C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.O>[Cl:1][C:2]1[CH:11]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:12][CH:13]([F:14])[F:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A cooled (−78° C.) solution of methyl 5-chloro-6-(difluoromethoxy)nicotinate (4.080 g; 17.17 mmol) in anh. toluene (110 ml) was treated dropwise with a solution of 1 M DIBAH in toluene (60.30 ml; 60.30 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 5 min., and then at 0° C. for 3 h. The obtained mixture was treated successively with water (55 ml), 1 M aq. NaOH (11 ml), and aq. sat. NaHCO3 (100 ml). The separated aq. layer was further extracted with Et2O (2×100 ml). The mixed organic layers were then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure affording (5-chloro-6-(difluoromethoxy)pyridin-3-yl)methanol as an orange oil. LC-MS (conditions A): tR=0.62 min.; [M+H]+: 210.25 g/mol.
Workup
- waitat 0° C. for 3 h
- extractionThe separated aq. layer was further extracted with Et2O (2×100 ml)
- dry with materialThe mixed organic layers were then dried over anh. MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-ebc0e76a901f400bb1f1307027175a23
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242970B2
Reaction notes
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