Ethanamine, 2,2,2-trifluoro- → 5-(benzyloxy)-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one

HRID 1519029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519029
[CH2:1]([O:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])O[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][C:18]([F:22])([F:21])[CH2:19][NH2:20]>Cl.C(O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[N:20]([CH2:19][C:18]([F:22])([F:21])[F:17])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 9773Ethanamine, 2,2,2-trifluoro-HCID 53141715-(Benzyloxy)-2-methyl-4H-pyran-4-one

Produkt 1

HCID 708051685-(benzyloxy)-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-oneAusbeute 84,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5-(Benzyloxy)-2-methyl-4H-pyran-4-one (4.32 g, 20.0 mmol) was mixed with trifluoroethylamine (6.92 g, 70.0 mmol) in 6N HCl (11.7 mL) and ethanol (5.8 mL). The reaction mixture was heated in a sealed flask at 100° C. for 20 hours. The mixture was then concentrated in vacuo and the residue was diluted with water. The solid was filtered, washed with water and ether to give 5-(benzyloxy)-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one (5.01 g) as white solid. Yield=84%; 1H NMR (MeOD-D4, 90 MHz) δ (ppm): 7.99 (s, 1H), 7.14-7.65 (m, 5H), 6.80 (s, 1H), 4.91-5.25 (m, 4H), 2.53 (s, 3H).

Aufarbeitung

  1. concentrationThe mixture was then concentrated in vacuo
  2. additionthe residue was diluted with water
  3. filtrationThe solid was filtered
  4. washwashed with water and ether

Quellen und Nachweise

ORD-Eintrag
ord-89ab953dff1f4f3a83ba40e9f672d192
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073865B2

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