Hydrochloric Acid → HCID 18441890, compound

To a solution of 3-[4-(trifluoromethyl)phenyl]propanoic acid (4.36 g, 20.0 mmol) in THF (100 ml) was added carbonyldiimidazole (3.89 g, 24.0 mmol) and the mixture was refluxed for 1 h. Into a separate flask was placed nitromethane (4.5 ml, 80.0 mmol), THF (40 ml) and sodium hydride (0.96 g, 24.0 mmol) and the mixture was stirred for 10 min. To this was added slowly the imidazolide from the first reaction and the mixture was refluxed for 16 h. To the reaction mixture was added water (100 ml) and the pH was adjusted to 3 with HCl. The THF was removed by rotary evaporation. The product was extracted with ethyl acetate. The product was purified by silica gel column chromatography (silica gel/30% ethyl acetate in petroleum ether) giving A as an oil (3.70 g, 71%). 1H NMR (300 MHz, CDCl3) δ 7.53 (dd, 2H), 7.28 (dd, 2H), 5.20 (s, 2H), 3.03 (m, 2H), 2.87 (m, 2H).

1. temperaturethe mixture was refluxed for 1 h
2. customInto a separate flask was placed
3. customfrom the first reaction
4. temperaturethe mixture was refluxed for 16 h
5. customThe THF was removed by rotary evaporation
6. extractionThe product was extracted with ethyl acetate
7. customThe product was purified by silica gel column chromatography (silica gel/30% ethyl acetate in petroleum ether)

ORD record

ord-1be5a899599e425083e25012931930ac

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07189851B2