Sodium → 4-methoxy-5-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazole
Reaction equation
[Na].[CH3:2][O-:3].[Na+].F[B-](F)(F)F.CO[N+:12]1[N:13]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[N:14]=[C:15]([CH3:17])[CH:16]=1>CO.O>[CH3:2][O:3][C:16]1[C:15]([CH3:17])=[N:14][N:13]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:26])[F:27])=[CH:22][CH:23]=2)[N:12]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
Sodium metal (0.25 g, 11.0 mmol) was stirred at 23° C. in methanol (10 mL) until a clear solution was obtained. This sodium methoxide solution was added to crude 1-methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazolium tetrafluoroborate (1:1) (i.e. the product of Step B, 1.1 g, 3.2 mmol). The reaction mixture was stirred at 23° C. for 6 h, during which time a white precipitate formed. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (40 mL, 10 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes to afford the title compound (0.82 g) as a colorless solid.
Workup
- customwas obtained
- customformed
- extractionextracted with ethyl acetate (40 mL, 10 mL)
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe crude residue was purified by chromatography on silica gel eluting with 0 to 10% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-ac5742b8a8a343139f74ad6f21cb8664
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302999B2
Reaction notes
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