Water → 1-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one

HRID 2213359

Reaktionsgleichung

Reaktionsgleichung von HRID 2213359
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH:15]=[C:14]([O:17][Si](C)(C)C)[CH2:13][CH2:12]1.C(=O)(OC)OCC=C.O>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:12]=[CH:13][C:14](=[O:17])[CH2:15][CH2:16]1

Komponenten

6

Edukt 3

HCID 962WaterHCID 534788Methyl 2-propen-1-yl carbonateHCID 218781391-(2-Fluoro-4-nitrophenyl)-4-[(trimethylsilyl)oxy]-1,2,3,6-tetrahydropyridine

Produkt 1

HCID 218776411-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-oneAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirring solution of the enol silyl ether from step 2 (100.0 g, 322 mmol) and allyl methyl carbonate (43.6 g, 386 mmol) in DMSO (625 ml) at ambient temperature is added Pd(OAc)2 (7.20 g, 32 mmol). The resulting solution is stirred under N2 at ambient temperature overnight. H2O (1 liter) is added and solvent allowed to cool to ambient temperature. The aqueous layer is extracted with EtOAc (2×800 ml) and the organic layers combined, washed with brine (800 ml) and organics dried over MgSO4. The solvent is removed and residue recrystallized from EtOAc/MTBE to afford 53.6 g (70%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ 2.71 (m, 2 H), 4.06 (m, 2 H), 5.41 (d, J=8 Hz, 1 H), 7.25 (m, 1 H), 7.35 (d, J=8 Hz, 1 H), 8.08 (m, 2 H); Anal. Calcd for C11H9FN2O3: C, 55.94; H, 3.84; N, 11.86; F, 8.04. Found: C, 55.82; H, 3.81; N, 11.67.

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous layer is extracted with EtOAc (2×800 ml)
  3. washwashed with brine (800 ml)
  4. dry with materialorganics dried over MgSO4
  5. customThe solvent is removed
  6. customresidue recrystallized from EtOAc/MTBE

Quellen und Nachweise

ORD-Eintrag
ord-6b34ba62f4ab449ab2bc221aaa5af471
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07105547B2

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