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Sodium hydride → ethyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclopropanecarboxylate

HRID 1772421
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1772421
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]([F:37])([F:36])[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[N:21][C:20]([C:23]3[CH:28]=[CH:27][C:26](/[CH:29]=[CH:30]/[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=3)=[N:19]2)=[CH:14][CH:13]=1>CS(C)=O>[F:37][C:10]([F:9])([F:36])[O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[N:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([CH:29]4[CH2:4][CH:30]4[C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:25][CH:24]=3)=[N:19]2)=[CH:14][CH:13]=1
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Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 90438191(E)-ethyl 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazol-3-yl)phenyl)acrylate

Produkt 1

HCID 90404224ethyl 2-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)cyclopropanecarboxylateAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679
Dimethyl Sulfoxide
Lösungsmittel

Versuchsvorschrift

To an oven-dried round bottomed flask was added sodium hydride (60% oil immersion, 0.380 g, 9.50 mmol) and anhydrous dimethyl sulfoxide (30 mL). Gas evolution occurred, and the solution was stirred at room temperature for 15 minutes. Trimethylsulfoxonium iodide (2.10 g, 9.54 mmol) was added, the flask neck was rinsed with anhydrous dimethyl sulfoxide (5 mL), and the reaction was stirred for 15 minutes. To the reaction was added (E)-ethyl 3-(4-(1-(4-(trifluoromethoxy)phenyl)-1 H-1,2,4-triazol-3-yl)phenyl)acrylate (C17) (3.22 g, 7.98 mmol) as a solid. The reaction was stirred at room temperature for 30 minutes, and then quenched with water and extracted with 1:1 ethyl acetate/hexanes (2×). The combined organic layers were washed with water (3×), dried over anhydrous sodium sulfate, filtered, and concentrated to afford the title compound as a yellow oil (1.50 g, 41%): 1H NMR (400 MHz, CDCl3) δ 8.55 (s, 1H), 8.10 (d, J=8.4 Hz, 2H), 7.80 (d, J=9.1 Hz, 2H), 7.39 (dd, J=6.6, 5.9 Hz, 2H), 7.20 (d, J=8.3 Hz, 2H), 4.19 (dt, J=14.0, 7.0 Hz, 2H), 2.64-2.52 (m, 2H), 1.97 (ddd, J=8.5, 5.3, 4.2 Hz, 1H), 1.71-1.61 (m, 1H), 1.42-1.32 (m, 1H), 1.29 (t, J=7.1 Hz, 3H); 19F NMR (376 MHz, CDCl3) δ −58.03; ESIMS m/z 418 ([M+H]+).

Aufarbeitung

  1. washthe flask neck was rinsed with anhydrous dimethyl sulfoxide (5 mL)
  2. stirringthe reaction was stirred for 15 minutes
  3. stirringThe reaction was stirred at room temperature for 30 minutes
  4. customquenched with water
  5. extractionextracted with 1:1 ethyl acetate/hexanes (2×)
  6. washThe combined organic layers were washed with water (3×)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-300498ae8ecd44abab8d69558ecccdd4
Quelldatensatz
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09249133B2

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