2-Bromopropane → HCID 15933238, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl thiol XXIIa(i) (1.50 mL, 13.2 mmol) in DMSO (8 mL) was added NaOMe (802 mg, 14.7 mmol) and isopropylbromide (0.62 mL, 6.54 mmol) at rt. The resulting cloudy solution was heated to 90° C. and stirred for 5 hrs at the same temperature. The reaction was quenched with water, extracted by ether, dried over MgSO4. The organic phase was concentrated to afford the crude sulfide. This sulfide was directly used for the next step. To a solution of the above crude sulfide in MeOH (30 mL) was added a solution of oxone (6.8 g, 11.0 mmol) in water (30 mL) at 0° C. The resulting cloudy solution was warmed to rt, then stirred for 5 hrs. The reaction mixture was concentrated using rotary evaporator, diluted with water, extracted with EtOAc. The organic layer was separated, dried over MgSO4, concentrated to afford the crude sulfone which was purified by flash chromatography (EtOAc:Hex=1:3 to 1:2) to give 594 mg (56% for 2 steps) of tert-butyl isopropyl sulfone XXIc(i)). Rf 0.36 (1:2-EtOAc:Hex); 1H NMR (400 MHz, CDCl3) δ 3.40 (m, 1H), 1.44 (s, 9H), 1.42 (d, J=6.8 Hz, 6H).

Provenance & Evidence