1,1,1-Trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one → 2-Benzyl-1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-ol
Reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].[CH2:20]([Mg]Cl)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1COCC1>[CH2:20]([C:3]([OH:17])([CH2:4][C:5]([C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6])[C:2]([F:1])([F:18])[F:19])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1Participants
4
Procedure
To a chilled (−70° C.) solution of 70 mg (0.25 mmol) of 1,1,1-trifluoro-4-(5-fluoro-2-methoxyphenyl)-4-methylpentan-2-one (Example 1) in 2.5 mL of anhydrous THF was added a 2.0 M solution of benzyl magnesium chloride in THF. The mixture was stirred for 30 minutes and then was quenched with 15 mL of saturated aqueous ammonium chloride and extracted with five 5 mL portions of EtOAc. The combined organic layers were washed with three 5 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude material was chromatographed on silica gel using hexanes to load the sample, and then eluted with hexanes and then EtOAc-hexanes (0.5:99.5, then 1:99) to afford 58 mg (62%) of the title compound as an oil.
Workup
- customwas quenched with 15 mL of saturated aqueous ammonium chloride
- extractionextracted with five 5 mL portions of EtOAc
- washThe combined organic layers were washed with three 5 mL portions of brine
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude material was chromatographed on silica gel
- washeluted with hexanes
Sources & evidence
- ORD record
- ord-a356144c643b45388e0d748faeb25e52
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07268152B2
Reaction notes
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