Ethyl Acetate → Ethyl 6-trifluoromethyl-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylate

HRID 393332

반응식

HRID 393332 반응식
[CH:1]([C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[NH:13]C(=O)C(C)(C)C)=O.[H-].[Li+].[F:22][C:23]([F:32])([F:31])/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(OCC)(=O)C>CS(C)=O>[F:10][C:9]([F:11])([F:12])[C:7]1[CH:8]=[C:3]2[C:4](=[CH:5][CH:6]=1)[NH:13][CH:24]([C:23]([F:31])([F:32])[F:22])[C:25]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:1]2

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 62714Lithium hydrideHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoateHCID 21883657N-[2-Formyl-4-(trifluoromethyl)phenyl]-2,2-dimethylpropanamide

생성물 1

HCID 21883618Ethyl 6-trifluoromethyl-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylate수율 5%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
30 °C

실험 절차

To a suspension of N-(2-formyl-4-(trifluoromethylphenyl)-2,2-dimethyl propanamide (Step 2) (921 mg, 3.7 mol) and lithium hydride (115 mg, 14.5 mmol) in dimethyl sulfoxide (10 mL) was added ethyl 4,4,4-trifluorocrotonate (2.83 g, 16.8 mmol) and the contents warmed to 30° C. for 4 hours. After the addition of ethyl acetate (50 mL), the reaction was washed with water (2×30 mL), saturated ammonium chloride solution (2×30 mL), dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford a yellow solid. The product was purified by flash chromatography (silica gel, eluant: ethyl acetate-hexanes, 1:9) to yield, upon concentration of the appropriate fractions, ethyl 6-trifluoromethyl-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylate as a yellow solid (65 mg, 5%): mp 138-139° C. 1H NMR (CDCl3/300 MHz) 7.67 (s, 1H), 7.26 (s, 1H), 7.04 (d, 1H, J=6.6 Hz), 6.62 (m, 1H), 5.14 (m, 1H), 4.60 (brs, 1H), 4.32 (m, 2H), 1.35 (t, 3H, J=7.0 Hz). ESHRMS m/z 338.0592 (M−H Calc'd 338.0616). Anal. Calc'd for C13H11F3NO2: C, 49.57; H, 3.27; N, 4.13; Found: C, 49.23; H, 2.81; N, 3.93.

후처리

  1. washthe reaction was washed with water (2×30 mL), saturated ammonium chloride solution (2×30 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customto afford a yellow solid
  6. customThe product was purified by flash chromatography (silica gel, eluant: ethyl acetate-hexanes, 1:9)

출처 및 근거

ORD 기록
ord-2c9c443a6dd94a0b886a2eb554d5ba73
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06806288B1

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