Acetic Anhydride → (E)-N-(4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-enyl)benzyl)acetamide

To a stirred solution of (E)-(2-chloro-4-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-1-en-1-yl)phenyl)methanamine (0.3 g, 0.8 mmol) in CH2Cl2 (10 mL) was added acetic anhydride (0.12 mL, 1.14 mmol), and TEA (0.217 mL, 1.52 mmol), and the resultant reaction mixture was stirred at ambient temperature for 6 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined CH2Cl2 layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; 30-50% EtOAc in hexane) afforded the title compound as a off-white solid (0.2 g, 60%) mp 107-109° C.; 1H NMR (400 MHz, CDCl3) δ 7.37 (m, 3H), 7.28 (m, 4H), 6.60 (d, J=16.0 Hz, 1H), 6.36 (dd, J=16.0, 8.0 Hz, 1H), 5.75 (br s, 1H), 4.46 (d, J=6 Hz, 2H), 4.01 (m, 1H), 2.11 (s, 3H); ESIMS m/z 402.00 ([M+H]+).

1. customthe resultant reaction mixture
2. extractionextracted with CH2Cl2
3. washThe combined CH2Cl2 layer was washed with brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated under reduced pressure
6. customPurification by flash column chromatography (SiO2, 100-200 mesh; 30-50% EtOAc in hexane)

ORD-Eintrag

ord-fd66db8134fc4891b77bd27c6c0953cb

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09226500B2