p-Toluenesulfonic acid → 3-Bromo-4-cyclopent-1-enyl-pyridine

HRID 523590Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 523590
CC1C=CC(S(O)(=O)=O)=CC=1.[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1(O)[CH2:23][CH2:22][CH2:21][CH2:20]1.C(OCC)(=O)C>C1(C)C=CC=CC=1.CCCCCC>[Br:12][C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[C:19]1[CH2:23][CH2:22][CH2:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 6101p-Toluenesulfonic acidHCID 8857Ethyl AcetateHCID 70982889HCID 70982889, Verbindung

Produkt 1

HCID 709821203-Bromo-4-cyclopent-1-enyl-pyridineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

PTSA (819 mg, 4.315 mmol) was added portionwise to a stirred mixture of 1-(3-bromo-pyridin-4-yl)-cyclopentanol (I-34a: 520 mg, 2.15 mmol) in 25 mL of toluene. The resulting mixture was heated to reflux at 120° C. for 4 hours. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was concentrated, basified with aqueous sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with water, brine solution, dried over anhydrous sodium sulphate and concentrated to afford the crude product. Purification by column chromatography on silica gel (8% ethyl acetate in hexane) afforded 350 mg of the product (73% yield).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. concentrationThe reaction mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water, brine solution
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated
  7. customto afford the crude product
  8. customPurification by column chromatography on silica gel (8% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-88d3e6018d424e7d9c6a9972636fa12b
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09339501B2

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