Ethanol → 1,1-Diethoxy-3-[4-(trifluoromethyl)phenyl]propan-2-one
Reaction equation
[N+](=[CH:3][C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)=[N-].Cl[O:18][C:19]([CH3:22])(C)C.[CH2:23]([OH:25])[CH3:24]>>[CH2:23]([O:25][CH:3]([O:18][CH2:19][CH3:22])[C:4](=[O:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][CH:7]=1)[CH3:24]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Under an argon atmosphere, 1-diazo-3-[4-(trifluoromethyl)phenyl]propan-2-one (53) (661 mg, 2.90 mmol) was dissolved in anhydrous ethanol (6 mL) and cooled to 0° C. To this was added tert-butyl hypochlorite (330 μL, 2.92 mmol) and stirred for an hour at the same temperature. After being concentrated under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate═18/1) to give 1,1-diethoxy-3-[4-(trifluoromethyl)phenyl]propan-2-one (54) as a colorless oily substance (544 mg, 1.87 mmol, 64.7%).