4-Toluenesulfonyl chloride → HCID 59855794, compound

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Reaction Steps

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).

Provenance & Evidence