Butyn-2-one → HCID 131718379, compound

Participants

Reaction Steps

To a stirred solution of 2-mercaptothiazoline (3.7 g., 0.03 mole) in aqueous ethanol (35 ml) at 35° C., a solution of 3-butyn-2-one (2.0 g., 0.03 mole) in ethanol (10 ml) was added dropwise over 10 minutes. The resulting solution was refluxed for 2 hours and stirred at ambient temperature for 18 hours. The volatiles were removed in vacuo and the residue was extracted into ethyl acetate and washed thoroughly with water. After drying (MgSO4), the solution was concentrated to an amber oil consisting of the cis and trans isomers. Purification and isolation of the isomers was accomplished via column chromatography on silica gel using hexanes/ethyl acetate (4:1), yielding 2.7 g cis-isomer as a white solid, mp 69°-72° C. IR.(nujol) uc=o 1660 cm-1. The trans-isomer was recovered as an amber oil, 0.2 g IR (neat) uc=o 1660 cm-1.

Provenance & Evidence