Potassium Sodium Tartrate → {5-Chloro-6-[(1,3-difluoropropan-2-yl)oxy]pyridin-3-yl}methanol
Reaction equation
[Cl:1][C:2]1[C:3]([O:12][CH:13]([CH2:16][F:17])[CH2:14][F:15])=[N:4][CH:5]=[C:6]([CH:11]=1)[C:7](OC)=[O:8].CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:11]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:12][CH:13]([CH2:16][F:17])[CH2:14][F:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of methyl 5-chloro-6-[(1,3-difluoropropan-2-yl)oxy]nicotinate (1 g) in THF (20 mL) was added dropwise a 0.99 M solution of DIBAL in toluene (11.3 mL) at 0° C., followed by stirring at 0° C. for 2 hours. Then, the reaction solution was poured into an aqueous Rochelle salt solution, followed by stirring at room temperature for 1 hour. After extraction with an EtOAc-water system, the organic layer was washed with brine, dried over MgSO4, and then filtered, and the desiccant was removed. The vehicle was evaporated under reduced pressure, followed by purification by silica gel column chromatography (Hex:AcOEt=98:2 to 70:30) to obtain {5-chloro-6-[(1,3-difluoropropan-2-yl)oxy]pyridin-3-yl}methanol (650 mg) as a colorless liquid.
Workup
- stirringby stirring at room temperature for 1 hour
- extractionAfter extraction with an EtOAc-water system
- washthe organic layer was washed with brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customthe desiccant was removed
- customThe vehicle was evaporated under reduced pressure
- customfollowed by purification by silica gel column chromatography (Hex:AcOEt=98:2 to 70:30)
Sources & evidence
- ORD record
- ord-5705f60db6824d1f9f4b3e215f5a0ca1
- Source dataset
- uspto-grants-2012_06
- Patent number
- US08193378B2
Reaction notes
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