Trifluoroacetic acid → HCID 178486372, compound
Reaction equation
[CH3:1][O:2][C:3]1([C:9]2[N:10](COCC[Si](C)(C)C)[CH:11]=[C:12]([C:14]([F:17])([F:16])[F:15])[N:13]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.FC(F)(F)C(O)=O.[SiH](CC)(CC)CC>>[CH3:1][O:2][C:3]1([C:9]2[NH:10][CH:11]=[C:12]([C:14]([F:16])([F:15])[F:17])[N:13]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1Participants
4
Conditions
- Temperature
- 20 °C
Procedure
Into a 100-mL round-bottom flask, was placed 2-(4-methoxytetrahydro-2H-pyran-4-yl)-4-(trifluoromethyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (compound 217.1, 1.3 g, 3.42 mmol), trifluoroacetic acid (4 mL), Et3SiH (2 mL). The resulting solution was stirred overnight at 20° C., then quenched by the addition of 20 mL of water. The pH of the solution was adjusted to 8 with sodium hydroxide (1 M). The aqueous phase was extracted with 2×100 mL of ethyl acetate. The combined organic layers were washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. This resulted in 1 g (crude) of the title compound as a light yellow oil.
Workup
- customInto a 100-mL round-bottom flask, was placed
- customquenched by the addition of 20 mL of water
- extractionThe aqueous phase was extracted with 2×100 mL of ethyl acetate
- washThe combined organic layers were washed with 2×50 mL of brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-0081ac5efd7f4252bb13dbef9c521e21
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09428502B2
Reaction notes
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