Trifluoroacetic acid → HCID 57424237, compound
Reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[O:16][CH3:17])=O)[CH3:2].FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C(=O)(O)[O-].[Na+]>O.CCCCCC.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:18])[CH2:5][CH2:6][CH2:7][C:9]1[CH:14]=[CH:13][C:12]([Br:15])=[CH:11][C:10]=1[O:16][CH3:17])[CH3:2]Participants
Conditions
- Temperature
- 55 °C
Procedure
A solution of 4-(4-bromo-2-methoxy-phenyl)-4-oxo-butyric acid ethyl ester (Intermediate 60, 14.73 g, 46.8 mmol) in trifluoroacetic acid (72 mL, 935 mmol) was treated with triethylsilane (30 mL, 187 mmol) and the resulting reaction mixture was heated at 55° C. for 4 h. The reaction mixture was then cooled to ambient temperature, neutralized with solid sodium bicarbonate, diluted with water and extracted with diethyl ether. The organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford a residue that was subjected to flash column chromatography over silica gel (230-400 mesh) using 8% ethyl acetate in hexane as the eluent to afford the title compound (7.4 g, 53%) as a colorless oil.
Workup
- customthe resulting reaction mixture
- temperatureThe reaction mixture was then cooled to ambient temperature
- extractionextracted with diethyl ether
- washThe organic phase was washed with water and brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated in vacuo
- customto afford a residue that
Sources & evidence
- ORD record
- ord-e315394c883c4ce1b302bb5f64ce2506
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07468391B2
Reaction notes
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