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

HRID 495729Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 495729
[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. custompurified by column chromatography (silica gel, developing solvent: hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9e7ea9585996434eafaa9b2815ea51f1
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06939928B1

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