Isoprene → 11,11-Diphenylundec-1-ene

HRID 275466Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 275466
[Li].[C:2]1([C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(OC)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=CC(=C)C.[Cl-].[NH4+]>N.C1COCC1.CO>[C:2]1([CH:8]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH:17]=[CH2:18])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 4

HCID 6557IsopreneHCID 25517Ammonium ChlorideHCID 3028194Lithium2×HCID 2008832511,11-Diphenyl-11-methoxyundec-1-ene

Produkt 1

HCID 2008832411,11-Diphenylundec-1-eneAusbeute 105,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 222AmmoniaLösungsmittel2×HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium wire, 0.75 g, was dissolved in 300 mL of ammonia at -78° C. A solution of 10.1 g of 11,11-diphenyl-11-methoxyundec-1-ene in 20 mL of THF was added to the lithium solution and the mixture was stirred at reflux for 30 min. To a reaction vessel were added sequentially 5 mL isoprene, 5 mL of methanol, and 10 g of ammonium chloride and the ammonia allowed to evaporate at room temperature. Diethyl ether was added to the mixture and the solution was washed with water and brine (saturated aqueous sodium chloride). The organic layer was dried and concentrated in vacuo to give 9.7 g of 11,11-diphenylundec-1-ene which is characterized by:

Aufarbeitung

  1. temperatureat reflux for 30 min
  2. customto evaporate at room temperature
  3. additionDiethyl ether was added to the mixture
  4. washthe solution was washed with water and brine (saturated aqueous sodium chloride)
  5. customThe organic layer was dried
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c2a041d3d50a45569ae316ceded2d739
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393795

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