5-(4-Fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone → 4-(4-Fluoro-benzyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione

HRID 1631885Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1631885
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH:7]2[C:11](=[O:12])[C:10]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[C:9]([O:22]C)[CH2:8]2)=[CH:4][CH:3]=1>CC(C)=O.Cl>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][CH:7]2[CH2:8][C:9](=[O:22])[CH:10]([C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])[C:11]2=[O:12])=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 668682345-(4-Fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone

Produkt 1

HCID 668680864-(4-Fluoro-benzyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dioneAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 313Hydrochloric AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of 5-(4-fluoro-benzyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (136 mg, 0.40 mmol) in acetone (2 ml) is added a 2N solution of hydrochloric acid (2 ml) and the resulting solution is heated to 40° C. by microwave irradiation for 30 minutes. The reaction mixture is diluted with 2N hydrochloric acid (25 ml), and extracted with ethyl acetate (2×25 ml). The combined organics are washed with brine (25 ml), dried over magnesium sulphate, filtered and concentrated in vacuo to give 4-(4-fluoro-benzyl)-2-(2,4,6-trimethyl-phenyl)-cyclopentane-1,3-dione (124 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate (2×25 ml)
  2. washThe combined organics are washed with brine (25 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1529d5ab2a904ecf94937effc348343b
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791303B2

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