Diethyl Ether → (3,3-Dimethyl-cyclohex-5-en-1-yliden)-pent-4-ene

HRID 444377

Reaktionsgleichung

Reaktionsgleichung von HRID 444377
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Br-].[PH4+].[CH3:8][C:9]1([CH3:16])[CH2:14][CH:13]=[CH:12][C:11](=O)[CH2:10]1.[CH2:17](OCC)C>>[CH3:8][C:9]1([CH3:16])[CH2:14][CH:13]=[CH:12][C:11](=[CH:4][CH2:3][CH2:2][CH:1]=[CH2:17])[CH2:10]1

Komponenten

5

Edukt 4

HCID 3283Diethyl Ether3×HCID 1383222-Cyclohexenone, 5,5-dimethyl-HCID 21868956Phosphanium bromideHCID 178418339Butyllithium

Produkt 1

HCID 73683920(3,3-Dimethyl-cyclohex-5-en-1-yliden)-pent-4-eneAusbeute 50 %

Versuchsvorschrift

8 g of a 14% solution of butyl-lithium in diethylether were added under nitrogen within 15 min. to a suspension of 7 g of the above said phosphonium bromide in 80 ml ether. To the red resulting solution, cooled to 5°-10°, 2.1 g of 3,3-dimethyl-cyclohex-5-en-1-one in 10 ml ether, were added, whereupon, the reaction mixture was stirred for 3 h, filtered and the clear filtrate was washed with water until neutrality. On evaporation and distillation in a bulb apparatus, 1.5 g (50% yield) of (3,3-dimethyl-cyclohex-5-en-1-yliden-)-pent-4-ene were obtained.

Aufarbeitung

  1. temperatureTo the red resulting solution, cooled to 5°-10°
  2. filtrationfiltered
  3. washthe clear filtrate was washed with water until neutrality
  4. customOn evaporation and distillation in a bulb apparatus

Quellen und Nachweise

ORD-Eintrag
ord-aae513672bd44ebca849c88856bc1a5d
Quelldatensatz
uspto-grants-1981_04
Patentnummer
US04264467

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