Oxygen → 4-(1-methoxytridecyl)-5-hydroxy-2(5H)-furanone

Participants

Reaction Steps

A mixture of 4-(1-methoxytridecyl)-2-trimethylsilylfuran (280 mg, 0.8 mmol) and Rose Bengal (5 mg) in tetrahydrofuran (7 ml) was exposed to singlet oxygen for 5 hours at -78 degrees. The residue, after solvent removal, was flash chromatographed on silica using 60% ethyl ether/petroleum ether. Fractions with Rf of about 0.21 on evaporation afforded the 4-(1-methoxytridecyl)-5-hydroxy-2(5H) -furanone as a colorless prism: mp 53-4 degrees.

Provenance & Evidence