Triethylamine → 2-n-Heptylthio-4-tetrahydropyranyloxycyclopent-2-en-1-one

Participants

Reaction Steps

2,3-Epoxy-4-tetrahydropyranyloxycyclopentan-1-one (200 mg) and 121 mg of n-heptylmercaptan were dissolved in 5 ml of methanol, and 158 mg of triethylamine was added. The mixture was stirred at room temperature for 2 hours. The reaction mixture was poured into an aqueous solution of ammonium chloride, and extracted with ethyl acetate. The extract was treated by a customary procedure to afford 280 mg of a crude product. The crude product was chromatographed on a thin layer plate with cyclohexane/ethyl acetate (=6/4) to afford 80 mg of 2-n-heptylthio-4-tetrahydropyranyloxycyclopent-2-en-1-one in a yield of 26%. The product had the following characteristics.

Provenance & Evidence