4-Toluenesulfonyl chloride → HCID 59855794, compound

Ethyl 2-formyl-3-oxopropanoate (3.2 g, 22 mmol) in diethyl ether (25 mL) was teated with triethylamine (3.5 mL, 25 mmol) at about 0° C. The mixture was stirred at room temperature for about 1 h before the diethyl ether was removed in vacuo. To the residue was added a solution of p-toluenesulfonyl chloride (4.5 g, 23.6 mmol) in N,N-dimethylformamide (60 mL) at about 0° C. The mixture was stirred for about 5 h while being allowed to warm to room temperature. 3-Aminocyclopent-2-en-1-one (1.75 g, 18 mmol) was added and the mixture was heated to about 85-90° C. over night. The mixture was cooled to room temperature and was concentrated in vacuo. The residue was diluted with chloroform (200 mL), washed with sodium carbonate solution, filtered through Celite, and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using dichloromethane/methanol/ammonium hydroxide (95:4.5:0.5) as the mobile phase to provide the title compound: 1H NMR (300 MHz, CDCL3): δ 1.42 (t, J=8.0 Hz, 3H), 2.82 (t, J=8.0 Hz, 2H), 3.38 (t, J=8.0 Hz, 2H), 4.42 (q, J=8.0 Hz, 3H), 8.60 (s, 1H), 9.40 (s, 1H).

1. customwas removed in vacuo
2. temperaturethe mixture was heated to about 85-90° C. over night
3. temperatureThe mixture was cooled to room temperature
4. concentrationwas concentrated in vacuo
5. additionThe residue was diluted with chloroform (200 mL)
6. washwashed with sodium carbonate solution
7. filtrationfiltered through Celite
8. concentrationconcentrated under vacuum
9. customThe residue was purified by flash column chromatography on silica gel

ORD record

ord-bacedc7c4129485d9f0e889b80b2c855

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468371B2