Water → cis-Stilbene

HRID 351959

Reaktionsgleichung

Reaktionsgleichung von HRID 351959
[C:1]1([C:7]#[C:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.O>C1COCC1.Cl[Ti](Cl)(Cl)Cl>[C:1]1(/[CH:7]=[CH:8]\[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:1]1([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 10390DiphenylacetyleneHCID 178418339Butyllithium

Produkt 2

HCID 7647DibenzylAusbeute 0,4 %HCID 5356785cis-StilbeneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To the solution of one equivalent of TiCl4 (1.1 ml, 10 mmol) and 0.5 equivalent of diphenylacetylene (0.89g, 5 mmol) in THF (40 ml) at −78° C. 2 equivalents of n-butyllithium (12.5 ml, 20 mmol, 1.6M solution in hexane) was slowly added and the resulting red-brown reaction mixture stirred at −78° C. for 1 h. The reaction mixture was then allowed to warm up to room temperature over 0.5 h followed by hydrolysis with 20 ml of H2O. Extraction of the organic products was accomplished with ether anhydrous ether. cis-Stilbene (91%) and bibenzyl (0.4%) were obtained as the products.

Aufarbeitung

  1. customat −78° C
  2. temperatureto warm up to room temperature over 0.5 h
  3. extractionExtraction of the organic products

Quellen und Nachweise

ORD-Eintrag
ord-d67bda8ade0d4492bd4b4a67d4973573
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743872B1

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