Boron trifluoride etherate → 4'-Isobutyl-2-ethoxyacetophenone
Reaction equation
I(C1C=CC=CC=1)=O.B(F)(F)F.[CH3:13][CH2:14][O:15]CC.[CH2:18]([C:22]1[CH:34]=[CH:33][C:25]([C:26]([O:28][Si](C)(C)C)=[CH2:27])=[CH:24][CH:23]=1)[CH:19]([CH3:21])[CH3:20]>C(O)C>[CH2:18]([C:22]1[CH:34]=[CH:33][C:25]([C:26](=[O:27])[CH2:28][O:15][CH2:14][CH3:13])=[CH:24][CH:23]=1)[CH:19]([CH3:21])[CH3:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
Iodosylbenzene (2.18 g) was dissolved in ethanol (45 ml), and boron trifluoride etherate (2.55 g) was added. The mixture was stirred at -70° C., and then 4-isobutyl-α-trimethylsilyloxystyrene (2.24 g) was added. The mixture was stirred at -70° C. for 30 minutes, and then the temperature was slowly raised to room temperature. The ethanol was evaporated and water was added. The mixture was neutralized with aqueous sodium bicarbonate. The mixture was extracted with dichloromethane, and the organic phase was dried over magnesium sulfate, and concentrated. The residue was chromatographed on silica gel column eluting with hexane-ethyl acetate (94:6) to give 4'-isobutyl-2-ethoxyacetophenone (1.90 g) as an oil.
Workup
- stirringThe mixture was stirred at -70° C. for 30 minutes
- temperaturethe temperature was slowly raised to room temperature
- customThe ethanol was evaporated
- additionwater was added
- extractionThe mixture was extracted with dichloromethane
- dry with materialthe organic phase was dried over magnesium sulfate
- concentrationconcentrated
- customThe residue was chromatographed on silica gel column
- washeluting with hexane-ethyl acetate (94:6)
Sources & evidence
- ORD record
- ord-c02c15bab89549f2a66521019a2194e4
- Source dataset
- uspto-grants-1994_08
- Patent number
- US05334716
Reaction notes
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