Cesium carbonate → HCID 70664333, compound

Participants

Reaction Conditions

Reaction Steps

(S)-3-Hydroxypyrrolidin-2-one (1.52 g, 15.0 mmol), 3-bromotoluene (2.57 g, 15.0 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.26 g, 0.45 mmol), palladium(II) acetate (0.067 g, 0.30 mmol) and cesium carbonate (7.33 g, 22.5 mmol) were mixed together in dioxane (50 mL) and stirred overnight at 80° C. overnight. The reaction mixture was washed with water (150 mL), and the aqueous layer was extracted with dichloromethane (3×150 mL). The combined organic layers were dried (sodium sulfate) and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.47 (s, 1H), 7.42 (d, J=8.3 Hz, 1H), 7.26 (t, J=7.9 Hz, 1H), 7.00 (d, J=7.6 Hz, 1H), 4.81 (d, J=3.1 Hz, 1H), 4.56-4.49 (m, 1H), 3.80-3.70 (m, 2H), 2.60-2.53 (m, 1H), 2.37 (s, 3H), 2.16-2.06 (m, 1H).

Provenance & Evidence