Ethylene Glycol → HCID 12426260, compound

Participants

Reaction Steps

p-Toluenesulfonic acid (0.29 g, 1.51 mmol) was added to a solution of ketone (VII-l) (2.30 g, 15.11 mmol) in ethylene glycol (3.75 g, 60.45 mmol)—toluene (75 mL) and the reaction mixture was refluxed for 2 h using a Dean-Stark apparatus. The reaction mixture was allowed to cool to RT and was poured into a saturated solution of NaHCO3 (100 mL). The mixture was extracted with EtOAc (3×150 mL), dried (MgSO4) and concentrated. The crude product was purified by SGC using EtOAc:hexane=3:1 (v/v) as the eluent to give (VII-m) (2.33 g, 78%) as a white solid; 1H NMR (400 MHz, CDCl3) δ 1.68-1.84 (m, 6H), 2.26-2.34 (dd, J=6.6 and 18.4 Hz, 2H), 2.40-2.48 (m, 4H), 3.77-3.81 (m, 2H), 3.85-3.89 (m, 2H).

Provenance & Evidence