3-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoate → 3-(2,4-Dioxocyclohexyl)propyl 2-(methylamino)benzoate

HRID 77272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 77272
[CH3:1][NH:2][C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][C:14]([O:17]CC)=[CH:13][C:12]1=[O:20])=[O:6]>C(Cl)Cl.C(OCC)C>[CH3:1][NH:2][C:3]1[CH:24]=[CH:23][CH:22]=[CH:21][C:4]=1[C:5]([O:7][CH2:8][CH2:9][CH2:10][CH:11]1[CH2:16][CH2:15][C:14](=[O:17])[CH2:13][C:12]1=[O:20])=[O:6]

Komponenten

3

Edukt 1

HCID 252417523-(4-Ethoxy-2-oxocyclohex-3-enyl)propyl 2-(methylamino)benzoate

Produkt 1

HCID 115149903-(2,4-Dioxocyclohexyl)propyl 2-(methylamino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881112Ethyl ether methylene chlorideLösungsmittel

Versuchsvorschrift

Compound 4 was stirred in a mixture of THF/3N HCl (1/1) at rt for 3 h and the mixture was concentrated. The crude product was washed with EtOAc/hexane/MeOH (1/2/0.5) to afford 6 as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.83 (1H, m), 7.34 (1H, m), 6.55 (2H, m), 4.22 (2H, t, J=6.3 Hz), 3.60 (2H, m), 2.84 (3H, s), 2.52-1.50 (9H, m); 13C NMR (75 MHz, CDCl3) δ 204.3, 203.8, 168.6, 151.6, 134.9, 131.7, 131.5, 115.2, 111.6, 110.5, 64.1, 58.4, 49.1, 39.9, 30.1, 26.4, 26.0, 24.7; ESI MS m/z 326 (M++Na+).

Aufarbeitung

  1. concentrationthe mixture was concentrated
  2. washThe crude product was washed with EtOAc/hexane/MeOH (1/2/0.5)

Quellen und Nachweise

ORD-Eintrag
ord-80472e5452bb4098997e033a23afc741
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841132B2

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