Dimethyl Sulfide → HCID 86656221, compound

Participants

Reaction Conditions

Reaction Steps

Allyloxy-phenyl-acetic acid methyl ester (described in EJOC 2000, 3145-3163; 3 g, 14.5 mmol) was dissolved in dichloromethane (300 mL) and cooled to −75° C. O3 was blubbled through the solution for 6 hours until the solution turned blue. Argon was blubbled through the solution for 1 hour, then dimethyl sulfide (9.04 g, 10.8 mL, 145 mmol) was added to the reaction mixture and kept at room temperature for 12 hours. The reaction mixture was evaporated and the residue purified by flash chromatography over 50 g SiO2-flash pack using gradient 10-100% EtOAc in heptane over 60 minutes to give the title compound as light yellow oil (2.72 g, 90%).

Provenance & Evidence