5-Trifluoromethylthiophene-3-one → 4-methyl-2-[4-(trifluoromethyl)phenyl]-5-[[5-(trifluoromethyl)-3-thienyl]oxy]-2H-1,2,3-triazole
Reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]([F:16])([F:15])[C:9]1[S:13][CH2:12][C:11](=[O:14])[CH:10]=1.F[B-](F)(F)F.CO[N+:24]1[N:25]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)[N:26]=[C:27]([CH3:29])[CH:28]=1>C(#N)C.O>[CH3:29][C:27]1[C:28]([O:14][C:11]2[CH:10]=[C:9]([C:8]([F:16])([F:15])[F:7])[S:13][CH:12]=2)=[N:24][N:25]([C:30]2[CH:31]=[CH:32][C:33]([C:36]([F:38])([F:37])[F:39])=[CH:34][CH:35]=2)[N:26]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 23 °C
Procedure
Potassium tert-butoxide (0.30 g, 2.6 mmol) and 5-trifluoromethylthiophene-3-one (0.44 g, 2.6 mmol) were dissolved in acetonitrile (4 mL). A solution of crude 1-methoxy-4-methyl-2-[4-(trifluoromethyl)phenyl]-2H-1,2,3-triazolium tetrafluoroborate (1:1) (i.e., the product of Example 1, Step B, 0.70 g, 2.0 mmol) in acetonitrile (4 mL) was added at once. The reaction mixture was stirred at 23° C. for 27 h. The reaction mixture was diluted with water (20 mL) and extracted with diethyl ether (2×25 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 5% ethyl acetate in hexanes to afford the title compound (0.105 g) as a colorless solid.
Workup
- extractionextracted with diethyl ether (2×25 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 5% ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-3e1edb8ca99f4364b81bdc433ceda548
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09302999B2
Reaction notes
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