Trifluoroacetic acid → ethyl 6-chloro-7-(thien-2-ylmethyl)-2-(trifluoromethyl)-2H-chromene-3-carboxylate
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH:12](O)[C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[O:8][CH:7]([C:19]([F:22])([F:21])[F:20])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[O:8][CH:7]([C:19]([F:22])([F:21])[F:20])[C:6]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5]2Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
The crude oil from Example 170 Step 2 was dissolved in I mL of DCM. To this solution was added triethylsilane (41 μL, 0.26 mmol) and 20 μL of TFA and stirred at 25° C. After 24 h, the solution was stirred vigorously with solid NaHCO3 and H2O, which quenched the reaction. Stirring was stopped after 5 min, and the solution was allowed to separate into layers. The reaction mixture stood in this state for one day prior to workup. The organic layer was dried over MgSO4, filtered, and evaporated under reduced pressure to give an orange oil. The crude product was purified by flash chromatography to give reasonably pure compound.
Workup
- customquenched
- customthe reaction
- stirringStirring
- waitwas stopped after 5 min
- customto separate into layers
- waitThe reaction mixture stood in this state for one day
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- customevaporated under reduced pressure
- customto give an orange oil
- customThe crude product was purified by flash chromatography
- customto give reasonably pure compound
Sources & evidence
- ORD record
- ord-6564b16ceebd4588b55659a63816c4bf
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07259266B2
Reaction notes
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