Toluene → 2-(5-Bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

HRID 40479

Reaktionsgleichung

Reaktionsgleichung von HRID 40479
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.C1(C)C=CC=CC=1.C([O-])(=O)C.C([O-])(=O)C.C([O-])(=O)C.[Br:27][C:28]1[CH:29]=[CH:30][C:31]([CH:35]2[CH2:37][CH2:36]2)=[C:32]([Pb+3])[CH:33]=1>CN(C)C1C=CN=CC=1.C(Cl)(Cl)Cl.ClCCl.Cl>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([CH:35]2[CH2:37][CH2:36]2)=[C:30]([CH:2]2[C:3](=[O:6])[CH2:4][CH2:5][C:1]2=[O:7])[CH:29]=1

Komponenten

8

Edukt 3

HCID 1140TolueneHCID 774661,3-CyclopentanedioneHCID 178419342HCID 178419342, Verbindung

Produkt 1

HCID 666768602-(5-Bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 6212ChloroformLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of cyclopentane-1,3-dione (0.57 g, 0.0058 mol) and 4-dimethylaminopyridine (3.64 g, 0.030 mol) in chloroform (33 ml) is added toluene (9 ml) then 5-bromo-2-cyclopropylphenyl lead triacetate (3.77 g, 0.0065 mol). This solution is heated at 80° C. for 20 hours then cooled to room temperature and diluted with dichloromethane and 2M aqueous hydrochloric acid. The resulting biphasic suspension is filtered through diatomaceous earth and the two phases are separated. The organic layer is further washed with 2M aqueous hydrochloric acid and the aqueous phase is extracted again with dichloromethane. All organic fractions are combined, washed with brine, dried over magnesium sulfate then concentrated in vacuo. The crude product is finally purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant) to afford 2-(5-bromo-2-cyclopropylphenyl)cyclopentane-1,3-dione as a pale yellow solid.

Aufarbeitung

  1. temperaturethen cooled to room temperature
  2. filtrationThe resulting biphasic suspension is filtered through diatomaceous earth
  3. customthe two phases are separated
  4. washThe organic layer is further washed with 2M aqueous hydrochloric acid
  5. extractionthe aqueous phase is extracted again with dichloromethane
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationthen concentrated in vacuo
  9. customThe crude product is finally purified by flash column chromatography on silica gel (isohexane/ethyl acetate eluant)

Quellen und Nachweise

ORD-Eintrag
ord-34572c46811e4ecc907e60bca4b397f0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530388B2

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