1-Nitropropane → HCID 54775374, compound

Participants

Reaction Steps

To a 0° C. solution of 3-(pyrrolidin-1-yl)pent-2-enoate (3.4 g, 17.2 mmol), 1-nitropropane (2.0 mL, 22.2 mmol), and triethylamine (7.5 mL, 53.4 mmol) in anhydrous chloroform (20 mL) was added a solution of phosphoryl trichloride (4.0 mL, 42.9 mmol) in anhydrous chloroform (6 mL) via syringe pump (1 hour). The reaction mixture was allowed to warm to room temperature and stirred overnight. The mixture was then stirred at reflux for 1 hour. After cooling to room temperature, the mixture was extracted with water (3×20 mL), 2 N HCl (2×20 mL), and brine (1×20 mL). The organic layer was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-15% ethyl acetate/hexane), affording ethyl 3,5-diethyl-1,2-oxazole-4-carboxylate (830 mg, 25%).

Provenance & Evidence