Diisobutylaluminum hydride → [6-(Difluoromethoxy)pyridin-2-yl]methanol
Reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[N:9]=[C:8]([C:10](OC)=[O:11])[CH:7]=[CH:6][CH:5]=1.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[N:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][CH:5]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A cooled (−78° C.) solution of methyl 6-(difluoromethoxy)picolinate (4.310 g; 21.21 mmol) in anh. toluene (120 ml) was treated dropwise with a solution of 1 M DIBAH in toluene (63.60 ml; 63.60 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 (6-(difluoromethoxy)pyridin-2-yl)methanol as a yellow oil (3.310 g; 89%). LC-MS (conditions D): tR=0.76 min.; no ionisation.
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-955bd79727894b6892ed1db1060b6d5e
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242970B2
Reaction notes
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