m-Chloroperbenzoic acid → HCID 58381702, compound

Participants

Reaction Conditions

Reaction Steps

2-((3Z,6Z,9Z,12Z)-Pentadeca-3,6,9,12-tetraenylthio)butanoic acid (0.20 g, 0.62 mmol) was dissolved in dry CHCl3 (10 mL) and the solution was cooled down to −20° C. under inert atmosphere. mCPBA (˜77%, 0.15 g, 0.68 mmol) dissolved in dry CHCl3 (2 mL) was added dropwise and the resulting solution was stirred at −20° C. for 35 minutes. The solvents were evaporated in vacuo, the residue was added heptane (10 mL) and the resulting white precipitate was removed by filtration. The filtrate was concentrated in vacuo and the residue was added heptane (10 mL). The resulting white precipitate was again removed by filtration. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography on silica gel (heptane:EtOAc+w/1% HCOOH 4:1-1:1). Concentration of the appropriate fractions afforded 100 mg (48% yield) of the title compound as an oil.

Provenance & Evidence