Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone → 1-Phenyl-1-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]ethanol
Reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:27])[F:26])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][Mg]Br>C1COCC1>[C:1]1([C:7]([C:9]2[CH:10]=[N:11][C:12]3[C:17]([C:18]=2[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[CH:16][CH:15]=[CH:14][C:13]=3[C:25]([F:28])([F:26])[F:27])([OH:8])[CH3:29])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
Phenyl[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone (Example 1, 0.260 g, 0.688 mmol) was taken into THF (5 mL) and cooled to 0° C. Next, methylmagnesium bromide (0.45 mL of 3.0 M solution in Ether, 1.35 mmol) was added and the reaction was allowed to stir overnight allowing to warm to room temperature. TLC indicated the starting material was still present, therefore additional methylmagnesium bromide was added and the reaction was heated at 50° C. overnight. The reaction was allowed to cool and was quenched with saturated NH4Cl and extracted with CH2Cl2 dried over sodium sulfate and concentrated. The product was purified via column chromatography using 10% ethyl acetate in hexane as the eluent to afford 0.176 g (64.8%) of desired product. MS (ESI) m/z 394 ([M+H]+); Anal. Calcd. for C24H18F3NO 0.5H2O: C, 71.63; H, 4.76; N, 3.48. Found: C, 71.45; H, 4.66; N, 3.09.
Workup
- temperatureto warm to room temperature
- temperaturethe reaction was heated at 50° C. overnight
- temperatureto cool
- customwas quenched with saturated NH4Cl
- extractionextracted with CH2Cl2
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customThe product was purified via column chromatography
Sources & evidence
- ORD record
- ord-c2ff112bdf95488ab4ae0c1859a58720
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576215B2
Reaction notes
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