HCID 68871843, compound → HCID 68872673, compound

Participants

Reaction Steps

2-(2-methyl-2-phenyl-pentanoyl)-malonic acid diethyl ester (2.45 g, 7.33 mmol) was stirred in methanesulfonic acid (20 mL) at 25° C. for 3 hours. The solution was partitioned cold water and ethyl acetate and the aqueous phase was extracted three times with ethyl acetate. The ethyl acetate layers were combined, dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane followed by 5%, 10%, and 20% ethyl acetate in hexane to give the title compound (1.34 g, 63%). 1H NMR (300 MHz, CDCl3) δ ppm 0.72 (m, 4 H) 0.96 (m, 1 H) 1.46 (m, 3 H) 1.63 (s, 3 H) 1.74 (m, 0.5 H) 1.92 (m, 0.5 H) 2.26 (m, 1 H) 4.47 (m, 2 H) 7.42 (m, 2 H) 7.59 (m, 1 H) 8.16 (m, 0.5 H) 8.23 (m, 0.5 H) 15.10 (s, 0.5 H) 15.16 (s, 0.5 H). (ESI+) m/z 289 (M+H)+.

Provenance & Evidence