Dimethyl Sulfide → HCID 131735404, compound

Participants

Reaction Conditions

Reaction Steps

Dimethylsulfane (2.0 mL, 26.74 mmol, 1.1 eq) was added drop wise at 0° C. to a stirred suspension of N-chlorosuccinimide (3.55 g, 26.74 mmol, 1.1 eq) in dichloromethane (20 mL). The mixture was cooled to −20° C., compound 336a) (8.0 g, 24.31 mmol, 1.0 eq) in dichloromethane (50 mL) was added drop wise at this temperature and the mixture was then stirred for 1 h at room temperature. The volatiles were evaporated and the residue was dissolved in xylene (30 mL) and stirred at 120° C. for 16 h. The solvent was removed in vacuo, ethyl acetate was added (50 mL), and the organic phase was washed with water (100 mL), dried over sodium sulfate and evaporated. The residue was purified by column chromatography [100-200 mesh silica, ethyl acetate/pet ether=1:4]. Yield: 5.5 g (60% of theory)

Provenance & Evidence