2-phenylpropane-2-thiol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 37.2 grams (0.200 mole) of O,O- diethyl phosphorodithioic acid, 30.5 grams (0.200 mole) of α,α-dimethyl α-toluenethiol and 16.5 ml. (0.220 mole) of methanol-free formalin is stirred vigorously at room temperature for 3 days. The mixture is extracted with 250 ml. of methylene chloride, and this solution is washed with two 30 ml. portions of saturated sodium chloride solution, four 30 ml. portions of 5% potassium hydroxide solution, and three 30 ml. portions of saturated sodium chloride. Evaporation of the solvent from the dried (magnesium sulfate) solution gives a colorless, moderately viscous liquid residue. The proton magnetic resonance spectrum of this material establishes that the desired product is the major component. The mixture is extracted with 250 ml of methylene chloride, and this solution is washed with two 30 ml Evaporation of the solvent from the dried (magnesium sulfate) solution gives a colorless, moderately viscous liquid residue

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 50 mL round bottom flask was added 1-thioxo-1,4-dihydro-2H-isoquinolin-3-one (250 mg, 1.41 mmol), and 2-phenylpropan-2-thiol (192 mg, 1.41) followed by a solution of TFA (10 mL, 20% v/v in DCM). The reaction mixture was stirred under Ar for 1 h, neutralized with NaHCO3 (100 mL, sat. aq.), and then extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4, and then the solvent was removed by rotary evaporation to yield a crude residue. The crude residue was purified via silica gel chromatography to provide the title compound as an orange solid (188 mg, 0.636 mmol, 45%). 1H NMR (400 MHz, CDCl3): δ ppm 8.11 (d, J=8.79 Hz, 1H), 7.55 (t, J=7.47 Hz, 3H), 7.42-7.50 (m, 1H), 7.14-7.29 (m, 5H), 6.74 (s, 1H), 1.95 (s, 6H). LC/MS m/z 296 [M+H]. extracted with EtOAc The organic phase was washed with brine dried over Na2SO4 the solvent was removed by rotary evaporation to yield a crude residue The crude residue was purified via silica gel chromatography