tert-Butyl mercaptan → HCID 66702460, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl thiol XXIIa(i) (1.51 mL, 13.3 mmol) in DMSO (7.2 mL) was added NaOMe (800 mg, 14.7 mmol) and cyclobutylbromide (0.63 mL, 6.47 mmol) at rt. The resulting cloudy solution was heated to 90° C. and stirred for 5 hr 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 (6.1 g, 9.82 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(XX(i)) which was recrystalized in hexanes to give 810 mg (71% for 2 steps) of tert-butyl cyclobutyl sulfone. 1H NMR (400 MHz, CDCl3) δ 3.92-4.01 (m, 1H), 2.62-2.73 (m, 2H), 2.20-2.28 (m, 2H), 1.94-2.14 (m, 2H), 1.36 (s, 9H).

Provenance & Evidence