反応 #82708

反応方程式

4-(4-trifluoromethyphenyl)-3-butene-2-one

1,3-cyclohexanedione

ammonium acetate

→

title compound

収率 56.9%

2-Methyl-4-(4-trifluoromethylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

収率 56.9%

溶媒

ethanol

反応条件

後処理

1. 1
   温度were heated
2. 2
   温度at reflux for eight hours
3. 3
   その他The solvent was evaporated
4. 4
   その他the residue was partitioned between water and ethyl acetate
5. 5
   その他The organic layer was dried
6. 6
   ろ過filtered
7. 7
   その他evaporated
8. 8
   その他to obtain a yellow oil
9. 9
   その他Chromatography, with hexane:ethyl acetate (1:1) as the eluent, and recrystallization from toluene

実験手順

A mixture of 4-(4-trifluoromethyphenyl)-3-butene-2-one (4.9 g), 1,3-cyclohexanedione (2.68 g), ammonium acetate (2.65 g) and 75 mL of ethanol were heated at reflux for eight hours and then cooled to room temperature. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and evaporated to obtain a yellow oil. Chromatography, with hexane:ethyl acetate (1:1) as the eluent, and recrystallization from toluene:hexane provided the title compound as a yellow solid (4.0 g); mp 116°-118° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.14-2.16 (m,2, CH2), 2.45-2.49 (m,2, CH2), 4.49 (d, 1, J=4.9, CH), 4.60 (d,1, J=4.9, CH), 7.35 (d,2, J=8.0, Ar), 7.57 (d,2, J=8.0, Ar), 8.54 (s,1, NH); (CI, CH4) MS: m/z=308(M+1); Analysis for Ci7H16F3NO: Calculated: C, 66.44; H, 5.25; N, 4.56; Found: C, 66.72; H, 5.34; N, 4.41.

出典