ETHYL-O-TOLYLKETONE

General procedure: A Schlenk tube (20 mL) charged with amide (0.5 mmol), PEPPSI (0.025 mmol, 5 molpercent), and K2CO3(2 equiv) was degassed and then refilled with nitrogen, three times. Then, solvent MTBE (6.0 mL)was added via syringe followed by 0.75 mL (1.5 equiv) borane solution (1 M in THF), which wascommercially available or was in situ prepared by hydroboration of olefin. The resulted mixture stirred for 24 h at room temperature under N2 atmosphere. The reaction was quenched with iced water(5 mL) and extracted with MTBE (2 x 5 mL). The combined MTBE extracts were dried over anhydrousNa2SO4. After filtration, solvents were removed by rotavapor to afford the crude product, which waspurified by flash column chromatography on silica gel using petroleum ether/EtOAc as the eluents.General procedure: The starting 1-(paratolyl)ethanol (1 mmol), chloramine-T (1 mmol), and In(OTf)3(0.3 mmol) were dissolved in CH3CN (10 mL) in a 100 mLflask equipped with a magnetic stirrer and a reflux condenser.The reaction mixture was heated at reflux for 3 h under anArgon atmosphere and was monitored for completion by TLC.After the reaction mixture was cooled to room temperature, the solvent was removed via rotary evaporation. The residueof the reaction mixture was separated through flash columnchromatography on silica gel. The obtained product was confirmed by spectroscopy.

Molecular Weight:148.20
XLogP3:2.4
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:2
Exact Mass:148.088815002
Monoisotopic Mass:148.088815002
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:140
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes