Reacción #331408

Ecuación de reacción

4-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one

3

3,3-Dimethoxy-cyclobutane-1,1-dicarboxylic acid diisopropyl ester

→

title compound

7-Chloro-2-phenyl-4-trifluoromethyl-quinoline

Disolventes

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONThe reaction was poured
2. 2
   OtroThe product precipitated
3. 3
   Filtraciónwas collected by suction filtration
4. 4
   Lavadowashed with water, and air
5. 5
   Otrodried overnight
6. 6
   Otrofrom aqueous quench
7. 7
   Lavadowere rinsed into a flask
8. 8
   Concentraciónconcentrated in vacuo
9. 9
   Otrochromatographed on silica gel with 3:1 Hexanes/methylene chloride

Procedimiento

4-(3-Chloro-phenylamino)-1,1,1-trifluoro-4-phenyl-but-3-en-2-one (2.8 g, 0.0086 mole) and polyphosphoric acid (60 mL) in a 250 mL 3 neck round bottom flask was stirred mechanically under an atmosphere of Nitrogen at 165° C. internal temperature for 3 h. The reaction was poured over stirring ice water (600 ml). The product precipitated, and was collected by suction filtration, washed with water, and air dried overnight. The solids remaining in the Buchner funnel, and beaker from aqueous quench were rinsed into a flask concentrated in vacuo, then combined with the filtered sample and chromatographed on silica gel with 3:1 Hexanes/methylene chloride to afford the title compound as a white solid; 1H NMR (CDCl3, 400 MHz) δ 7.53-7.59 (m, 3H), 7.60-7.63 (dd, 1H, J=2.2 & J=9.1 Hz), 8.06-8.09 (dq, 1H, J=1.9 & J=9.0 Hz), 8.16-8.20 (m, 3H), 8.29 (d, 1H, J=2.1 Hz); 19F NMR 8-61.48; MS (ES+): 308.0 (100) [MH+], 310.0 (30) [M+2H+].

Fuente