Butyn-2-one → HCID 131718379, compound

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.

1. temperatureThe resulting solution was refluxed for 2 hours
2. customThe volatiles were removed in vacuo
3. extractionthe residue was extracted into ethyl acetate
4. washwashed thoroughly with water
5. dry with materialAfter drying (MgSO4)
6. concentrationthe solution was concentrated to an amber oil
7. customPurification and isolation of the isomers
8. customyielding 2.7 g cis-isomer as a white solid, mp 69°-72° C
9. customThe trans-isomer was recovered as an amber oil, 0.2 g IR (neat) uc=o 1660 cm-1

ORD record

ord-702811520ab840e287dcaf69cb80e33a

Source dataset

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05302592