Methanol → 3-Pyridinemethanol, 5-chloro-6-(2,2,2-trifluoroethoxy)-
Reaction equation
[Cl:1][C:2]1[C:3]([O:13][CH2:14][C:15]([F:18])([F:17])[F:16])=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[Li+].[BH4-].CO>CCOCC>[Cl:1][C:2]1[CH:12]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][C:3]=1[O:13][CH2:14][C:15]([F:16])([F:17])[F:18]Participants
5
Conditions
- Temperature
- 40 °C
Procedure
To a solution of ethyl 5-chloro-6-(2,2,2-trifluoroethoxyl)nicotinate (7.51 g, 26.5 mmol) in Et2O (200 mL) was added LiBH4 (0.865 g, 39.7 mmol), followed by drop wise addition of methanol (1.611 ml, 39.7 mmol). The reaction was refluxed at 40° C. for one hour. The reaction mixture was then cooled to 0° C., and quenched with HCl (1M) until pH=2 for aqueous layer. The phases were separated and the aqueous layer was extracted with DCM (3×200 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (6.31 g). LCMS m/z 242.1 (M+H)+, Rt 0.77 min.
Workup
- temperatureThe reaction mixture was then cooled to 0° C.
- customquenched with HCl (1M) until pH=2 for aqueous layer
- customThe phases were separated
- extractionthe aqueous layer was extracted with DCM (3×200 mL)
- dry with materialThe organic was then dried (Na2SO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b3d4231668e745cbb8597b58c6a8beeb
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434719B2
Reaction notes
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