Acetone → 3-(1-Methyl-1-cyclohexyl)-6,6-dimethylfulvene

HRID 270988Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270988
[CH3:1][C:2]1([C:8]2[CH2:12][CH:11]=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:13][C:14]([CH3:16])=O.N1CCCC1>CO.CCOCC.O>[CH3:1][C:2]1([C:8]2[CH:12]=[CH:11][C:10](=[C:14]([CH3:16])[CH3:13])[CH:9]=2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Komponenten

7

Edukt 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 14688277(1-Methyl-1-cyclohexyl)cyclopentadiene

Produkt 1

HCID 146882823-(1-Methyl-1-cyclohexyl)-6,6-dimethylfulveneAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 2.71 g (16.7 mmol) of (1-methyl-1-cyclohexyl)cyclopentadiene in 30 ml of methanol, 25 ml (340.5 mmol) of acetone and 2.8 ml (33.5 mmol) of pyrrolidine were added with ice cooling, followed by stirring at room temperature for 3 days. After the reaction solution was diluted with 100 ml of ether, 50 ml of water was added. The organic phase was separated, washed with water and a saturated saline solution, then dried over anhydrous magnesium sulfate and filtered. From the filtrate, the solvent was removed under reduced pressure to obtain a liquid. The liquid was isolated and-purified by column chromatography (silica gel, developing solvent: hexane) to obtain 2.95 g (14.58 mmol) of a yellow liquid (yield: 87%). The analyzed values are given below.

Aufarbeitung

  1. additionwas added
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materiala saturated saline solution, then dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customFrom the filtrate, the solvent was removed under reduced pressure
  7. customto obtain a liquid
  8. customThe liquid was isolated
  9. custom-purified by column chromatography (silica gel, developing solvent: hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a6fdbfb9d70e4caa80ef6cd0c989963b
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449533B2

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