Ethyl vinyl ether → 1,1-Diphenyl-2-(1-ethenoxy)-hex-5-ene

HRID 1429014

Reaktionsgleichung

Reaktionsgleichung von HRID 1429014
[CH:1]([CH:14]1[CH2:19][C:18](=O)[CH:17]=[CH:16]O1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O-:24])(O)=O.[Na+].[CH:26](OCC)=C>[Hg](OC(C(F)(F)F)=O)OC(C(F)(F)F)=O>[C:2]1([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:14]([O:24][CH:21]=[CH2:26])[CH2:19][CH2:18][CH:17]=[CH2:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 8023Ethyl vinyl etherHCID 516892Sodium BicarbonateHCID 666308482-Benzhydryl-2H-pyran-4(3H)-one

Produkt 1

HCID 666312581,1-Diphenyl-2-(1-ethenoxy)-hex-5-eneAusbeute 66 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 16685285Hg(TFA)2Katalysator

Versuchsvorschrift

Into a mixture of 1,1-diphenyl-hex-5-en-2-ol 2 (7 g, 27.78 mmol) in ethyl vinyl ether (250 ml) was added Hg(OCOCF3)2 (2.37 g, 5.56 mmol) and was stirred overnight at room temperature. The reaction mixture was neutralized by addition of sat. aqueous NaHCO3. The organic phase was separated and the aqueous layer was extracted with ethyl ether, and dried over anhydrous Na2SO4. Removal of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 20:1) gave 1,1-diphenyl-2-(1-ethenoxy)-hex-5-ene 9 (5.1 g, 66%) as a liquid.

Aufarbeitung

  1. customThe organic phase was separated
  2. extractionthe aqueous layer was extracted with ethyl ether
  3. dry with materialdried over anhydrous Na2SO4
  4. customRemoval of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 20:1)

Quellen und Nachweise

ORD-Eintrag
ord-14e4ad4b54224bfb95a2cdb5c81ffd9f
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937189B2

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