Tetrahydrofuran → 1-(6-Chloro-2-methylpyridin-3-yl)-2,2,2-trifluoroethanol
Reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([CH3:10])[N:3]=1.O1CCCC1.C[Si](C)(C)[C:18]([F:21])([F:20])[F:19].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.[Cl-].[Na+].O>[Cl:1][C:2]1[N:3]=[C:4]([CH3:10])[C:5]([CH:6]([OH:7])[C:18]([F:21])([F:20])[F:19])=[CH:8][CH:9]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
6-Chloro-2-methylnicotinaldehyde (250 mg, 1.6 mmol) was added to tetrahydrofuran (10.7 ml) and cooled to 0° C. Trimethyl(trifluoromethyl)silane (0.3 ml, 1.9 mmol) was added followed by tetrabutylammonium fluoride (1.9 ml, 1.0M in THF, 1.9 mmol). The reaction mixture was allowed to warm to room temperature over 1 hour. The reaction was then diluted with water and brine and extracted with ethyl acetate (3×). The organic layers were combined and dried over magnesium sulfate, filtered, and concentrated in vacuo to yield the title compound as a solid.
Workup
- temperatureto warm to room temperature over 1 hour
- extractionextracted with ethyl acetate (3×)
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-1933638380db4105be44aae2d82dcffd
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08367706B2
Reaction notes
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