Methyl iodide → 2-Methyl-2-phenyl-cyclopentanone

HRID 1354093

Reaktionsgleichung

Reaktionsgleichung von HRID 1354093
[CH3:1]C(C)([O-])C.[K+].[C:7]1([CH:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.IC>C(O)(C)(C)C.O>[CH3:1][C:13]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:17][CH2:16][CH2:15][C:14]1=[O:18]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 2901542-PhenylcyclopentanoneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 3499412-Methyl-2-phenyl-cyclopentanoneAusbeute 89,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

2-Methyl-2-phenyl-cyclopentanone was prepared using the technique described by Ireland et al., J Org. Chem., 31, 2543 (1966). Potassium tert-butoxide (6.2 g, 55 mmol) was added to a solution of 2-phenylcyclopentanone (8.4 g, 53 mmol) in 100 mL of tert-butanol and the solution was stirred at room temperature for 45 min. Iodomethane (6 mL, 100 mmol) was added and after 2 hours the mixture was diluted with water and extracted twice with ether. The ether extract was washed with water and brine, dried (sodium sulfate) and evaporated. Purification of the residue by flash chromatography (5% ethyl acetate-hexane) afforded 8.3 g of 2-methyl-2-phenyl-cyclopentanone as an oil.

Aufarbeitung

  1. custom2-Methyl-2-phenyl-cyclopentanone was prepared
  2. extractionextracted twice with ether
  3. extractionThe ether extract
  4. washwas washed with water and brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated
  7. customPurification of the residue by flash chromatography (5% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d696319b263a43349f117dfb6fc784da
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07223767B2

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