Ethyl trifluoroacetate → HCID 71270874, compound

Temperature

-78 °C

To a mixture of 3-(2,3-dichlorophenyl)propanenitrile (100 mg, 0.5 mmol) in THF (20 mL) was added LDA (0.5 mL, 2 N in hexane, 1 mmol) dropwise at −78° C. under nitrogen. The mixture was stirred at −78° C. for 0.5 h. Then ethyl 2,2,2-trifluoroacetate (177.5 mg, 1.25 mmol) was added to the mixture dropwise. This solution was stirred at −78° C. for 5 h and diluted with sat. aq. ammonium chloride solution and 1N hydrochloric acid. This solution was extracted with EA (30 mL*3). The combined organic layers were washed with water and brine, dried over sodium sulphate, concentrated under reduced pressure. The residue was purified by a silica gel chromatography to give the titled product (82 mg, 55%) as a yellow solid; LC/MS: MS (ES+) m/e 296 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 3.03 (dd, J=12.9, 14.1 Hz, 1H), 3.52-3.60 (m, 2H), 7.20-7.32 (m, 2H), 7.43-7.51 (m, 1H).

1. stirringThis solution was stirred at −78° C. for 5 h
2. extractionThis solution was extracted with EA (30 mL*3)
3. washThe combined organic layers were washed with water and brine
4. dry with materialdried over sodium sulphate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by a silica gel chromatography

ORD record

ord-17bb4ae01daf49fe822eae266fede52f

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096605B2