Dimethyl Sulfide → HCID 69554694, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N-chlorosuccinimide (9.8 g, 73.1 mmol) in dichloromethane (25 ml) at −10° C. was added dropwise over 15 minutes dimethylsulfide (5.4 ml, 73.1 mmol). The mixture was stirred at −10° C. for 30 min, then a solution of 3-[(E)-3-hydroxy-1-methyl-1-propenyl]benzonitrile (from Preparation 33, 11.9 g, 69.6 nlmol) in dichloromethane (20 ml) was added dropwise over 15 minutes at −10° C. The mixture was stirred at 0° C. for 1 h, and was then poured onto saturated brine (50 ml). The layers were separated, and the aqueous layer was extracted with diethyl ether (2×50 ml). The extracts were combined, washed with water (50 ml), dried (MgSO4), filtered and concentrated in vacuo. The crude pale yellow oil (13.1 g, 100%) was used directly in the next step.

Provenance & Evidence