2-(3-Methoxyphenyl)-cyclopentanol → 2-(3-Methoxyphenyl)cyclopentan-1-one

HRID 418900

Reaktionsgleichung

Reaktionsgleichung von HRID 418900
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[OH:14])[CH:6]=[CH:7][CH:8]=1.[Cr](Cl)(O)(=O)=O.N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:13][CH2:12][CH2:11][C:10]2=[O:14])[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 27596482-(3-Methoxyphenyl)-cyclopentanolHCID 178526118HCID 178526118, Verbindung

Produkt 1

HCID 123629382-(3-Methoxyphenyl)cyclopentan-1-oneAusbeute 69.131,797 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-methoxyphenyl)-cyclopentanol (6.4 g, 0.033 mmoles) in 140 ml of methylene chloride, add a mixture of pyridine chlorochromate (14.4 g, 0.066 mmoles), and silica gel (14.4 g). After 1.5 hours, an equivalent amount of oxidizing agent and silica gel is added and the reaction is stirred an additional 3.5 hours. Reduce the solvent in half in vacuo at 35° C. and chromatograph on silica with 3-1 hexanes-ethyl acetate to yield 4.34 g of the titled compound. 1H NMR (CDCl3): 7.25 (m, 1H), 6.81-6.74 (m, 3H), 3.8 (s, 3H), 3.31 (m, 1H), 2.5 (m, 2H), 2.3 (m, 1H), 2.1 (m, 2H), 1.9 (m, 1H).

Aufarbeitung

  1. additionis added

Quellen und Nachweise

ORD-Eintrag
ord-738078e0ef6a4d98ad540e558f77b71f
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093302B2

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