1-Nitropropane → HCID 54775374, compound

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%).

1. stirringThe mixture was then stirred
2. temperatureat reflux for 1 hour
3. temperatureAfter cooling to room temperature
4. extractionthe mixture was extracted with water (3×20 mL), 2 N HCl (2×20 mL), and brine (1×20 mL)
5. customThe organic layer was recovered
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated
9. customdried in vacuo
10. customThe crude product was purified by flash chromatography (0-15% ethyl acetate/hexane)

ORD record

ord-7c7bcbf3be774175a23ce5a5e69e0481

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040538B2