Diisobutylaluminum hydride → (6-(Difluoromethoxy)pyridin-3-yl)methanol
Reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:13]=[CH:12][C:7]([C:8](OC)=[O:9])=[CH:6][N: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:5]=[CH:6][C:7]([CH2:8][OH:9])=[CH:12][CH:13]=1Participants
Conditions
- Temperature
- -78 °C
Procedure
A cooled (−78° C.) solution of methyl 6-(difluoromethoxy)nicotinate (4.700 g; 23.13 mmol) in anh. toluene (130 ml) was treated dropwise with a solution of 1 M DIBAH in toluene (69.40 ml; 69.40 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 then 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-3-yl)methanol as a yellow oil (3.758 g; 93%). LC-MS (conditions D): tR=0.71 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-d507fb326d8c44849fd3faa08ea5530c
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242970B2
Reaction notes
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