Ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate → HCID 178472336, Verbindung

HRID 604665Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604665
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]>CCOC(C)=O.[Pd]>[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]2[CH2:10][CH2:11][C@H:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:13][CH2:14]2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

4

Edukt 1

HCID 67057759Ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate

Produkt 1

HCID 178472336HCID 178472336, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(3-chloro-4-fluorophenyl)cyclohex-3-ene-1-carboxylate (270 mg, 0.955-mmoL) in EtOAc (15 mL) was added 10% Pd/C (45 mg). The reaction was put under an atmosphere of H2 (balloon) and stirred vigorously at room temperature. After 30 min, the catalyst was removed by filtration, and the filtrate was concentrated to afford a mixture of cis and trans products. The desired trans isomer was separated by flash chromatography on silica gel (0 to 10% EtOAc/hexanes) to afford ethyl trans-4-(3-chloro-4-fluorophenyl)cyclohexanecarboxylate. Rf=0.25 (5% EtOAc/hexanes). 1H NMR (500 MHz, CDCl3): δ 7.21 (d, J=7.3 Hz, 1H), 7.02-7.06 (m, 2H), 4-14 (q, J=7.1 Hz, 2H), 2.48 (m, 1H), 2.32 (m, 1H), 2.08-2.12 (m, 2H), 1.91-1.98 (m, 2H), 1.53-1.67 (m, 2H), 1.37-1.46 (m, 2H), 1.27 (t, J=7.1 Hz, 3H).

Aufarbeitung

  1. customthe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customto afford
  4. additiona mixture of cis and trans products
  5. customThe desired trans isomer was separated by flash chromatography on silica gel (0 to 10% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-7623c83a420a4f80a1d1061b4b24a641
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910592B2

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