Ethanol → Ethyl 2-[4-(2-methylpropyl)phenyl]propanoate
Reaction equation
[OH:1][C:2]([CH:4]([C:6]1[CH:15]=[CH:14][C:9]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH:8][CH:7]=1)[CH3:5])=[O:3].Cl[Si](C)(C)C.[CH3:21][CH2:22]O>>[CH2:10]([C:9]1[CH:8]=[CH:7][C:6]([CH:4]([CH3:5])[C:2]([O:1][CH2:21][CH3:22])=[O:3])=[CH:15][CH:14]=1)[CH:11]([CH3:12])[CH3:13]Participants
4
Procedure
To a solution of ibuprofen 1A (9.89g, 48 mmol) in anhydrous EtOH (35 mL) was added chlorotrimethylsilane (18.27 mL, 144 mmol) at room temperature, and the mixture was stirred at the same temperature for 2 h. After the removal of the excess EtOH and chlorotrimethylsilane under reduced pressure, the oily residue was treated with ice-cold saturated NaHCO3 (150 mL), and the resulting mixture was extracted with hexanes (450 mL). The hexanes solution was washed with brine (3×50 mL), and dried over anhydrous Na2SO2. Evaporation of the solvent afforded ethyl 2-(4′-isobutylphenyl)propionate 2A (11.24 g, in 100% yield) as a colorless oil.
Workup
- customAfter the removal of the excess EtOH and chlorotrimethylsilane under reduced pressure
- additionthe oily residue was treated with ice-cold saturated NaHCO3 (150 mL)
- extractionthe resulting mixture was extracted with hexanes (450 mL)
- washThe hexanes solution was washed with brine (3×50 mL)
- dry with materialdried over anhydrous Na2SO2
- customEvaporation of the solvent
Sources & evidence
- ORD record
- ord-e362cfd949764b52929b9a2b792f6b3e
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07049308B2
Reaction notes
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