3-Methyl-2-cyclopenten-1-one → 1-Tert-butyl-3-methylcyclopenta-1,3-diene

HRID 270982

Reaktionsgleichung

Reaktionsgleichung von HRID 270982
[C:1]([Mg]Cl)([CH3:4])([CH3:3])[CH3:2].[CH2:7](OCC)C.[CH3:12][C:13]1[CH2:17]C[C:15](=O)[CH:14]=1.[Cl-].[NH4+]>C(OCC)C.O>[C:1]([C:4]1[CH2:15][CH:14]=[C:13]([CH3:17])[CH:12]=1)([CH3:7])([CH3:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 176913-Methyl-2-cyclopenten-1-oneHCID 25517Ammonium ChlorideHCID 178467773HCID 178467773, Verbindung

Produkt 1

HCID 153198441-Tert-butyl-3-methylcyclopenta-1,3-dieneAusbeute 23.815,199 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution obtained by adding 350 ml of dehydrated diethyl ether to 450 ml (0.90 mol) of a tert-butylmagnesium chloride/diethyl ether solution (concentration: 2.0 mol/liter), a solution of 43.7 g (0.45 mmol) of 3-methylcyclopentenone in 150 ml of dehydrated diethyl ether was dropwise added in a nitrogen atmosphere at 0° C. with ice cooling, followed by stirring at room temperature for 15 hours. To the reaction solution, a solution of 80.0 g (1.50 mol) of ammonium chloride in 350 ml of water was dropwise added at 0° C. with ice cooling. To the resulting solution, 2500 ml of water was added, followed by stirring. Then, the organic phase was separated and washed with water. To the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling, followed by stirring at room temperature for 6 hours. The organic phase was separated from the reaction solution, washed with water, a saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered, and from the filtrate the solvent was distilled off to obtain a liquid. The liquid was subjected to vacuum distillation (45-47° C./10 mmHg) to obtain 14.6 g of a light yellow liquid. The analyzed values are given below.

Aufarbeitung

  1. customTo a solution obtained
  2. stirringby stirring
  3. customThen, the organic phase was separated
  4. washwashed with water
  5. additionTo the organic phase, 82 ml of a 10% hydrochloric acid aqueous solution was added at 0° C. with ice cooling
  6. stirringby stirring at room temperature for 6 hours
  7. customThe organic phase was separated from the reaction solution
  8. washwashed with water
  9. dry with materiala saturated sodium hydrogencarbonate aqueous solution, water and a saturated saline solution, and then dried over anhydrous magnesium sulfate
  10. filtrationThe drying agent was filtered
  11. distillationfrom the filtrate the solvent was distilled off
  12. customto obtain a liquid
  13. distillationThe liquid was subjected to vacuum distillation (45-47° C./10 mmHg)

Quellen und Nachweise

ORD-Eintrag
ord-01741cd0d5bb4765823685d2616c17aa
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449533B2

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