Diisobutylaluminum hydride → (2-(Difluoromethoxy)pyridin-4-yl)methanol
Reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][N:13]=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>[F:14][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([CH2:7][OH:8])[CH:11]=[CH:12][N:13]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A cooled (−78° C.) solution of methyl 2-(difluoromethoxy)isonicotinate (2.690 g; 13.24 mmol) in anh. toluene (60 ml) was treated dropwise with a solution of 1 M DIBAH in toluene (40.00 ml; 40.00 mmol), and the resulting mixture was further stirred at −78° C., under nitrogen, for 5 min., and then at 0° C. for 1.5 h. The obtained mixture was treated successively with water (55 ml), 1 M aq. NaOH (12 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 (2-(difluoromethoxy)pyridin-4-yl)methanol as a yellow oil. LC-MS (conditions A): tR=0.49 min.; [M+H]+: 176.37 g/mol.
Workup
- waitat 0° C. for 1.5 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-9bb8376c387c47f4b5082740ab0261bd
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242970B2
Reaction notes
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