Methanol → HCID 20380423, compound

Cyclopentenone (3.40 g) was oxidized in 15 ml of methanol using 4.4 ml of an aqueous solution of hydrogen peroxide and 4 ml of a 3 N aqueous solution of sodium hydroxide to afford crude 2,3-epoxycyclopentanone. To the crude product was added dropwise slowly 30 ml of a solution of 3.20 g of n-heptylmercaptan in methanol at room temperature over the course of 1.5 hours. Thirty minutes after the end of addition, the reaction mixture was concentrated under reduced pressure, and diethyl ether was added. The organic layer was washed with water, and treated in a customary manner to afford 5.21 g of a crude product. The crude product was chromatographed with cyclohexane/ethyl acetate (=8/2) to afford 2.50 g of 2-n-heptylthiocyclopent-2-en-1-one in a yield of 49%. The product had the following characteristics.

1. additionThirty minutes after the end of addition
2. concentrationthe reaction mixture was concentrated under reduced pressure, and diethyl ether
3. additionwas added
4. washThe organic layer was washed with water
5. additiontreated in a customary manner
6. customto afford 5.21 g of a crude product
7. customThe crude product was chromatographed with cyclohexane/ethyl acetate (=8/2)

ORD record

ord-c2cd794f341f48c5bf256b3492282961

Source dataset

uspto-grants-1979_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04180672